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Regular & Special Issues

24 data found. 1 - 24 listed

Published online: 24th July, 2017

Paper | Regular issue | Prepress
DOI: 10.3987/COM-17-13694
Copper Accelerated One-Pot Sequential Tandem Synthesis of Tetrahydropurinoisoquinoline Derivatives

Pradip Kumar Maji* and Ayan Mahalanobish

*Department of Chemistry, Bidhan Chandra College , Asansol, Burdwan, 713304, WB, India

Abstract

Copper catalyzed efficient and operationally simple tandem synthesis of purino[8,9-a]isoquinolinedione from 5,6-diamino-1,3-dimethyluracil and in situ generated alkenyl aldehyde has been described. In this cascade reaction C-C and C-N bonds are formed through Sonogashira coupling, 5-endo cyclization, and 6-endo cyclization in a same reaction vessel.

Supporting Info. (3.2MB)PDF (311KB)

Published online: 14th July, 2017

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13242
A New Fluorescence Chemosensor for Hg2+ Based on Carbazole and Thiourea

Fang-fang Yin, Wei-ju Zhu, Min Fang, Zhen-yu Wu, Ying Xu, Hai-lun Wang, Yao Wang, and Cun Li*

*School of Chemistry and Chemical Engineering & Anhui Province Key Laboratory of Environmental-friendly Polymer Materials, Anhui University, Hefei 230601, China

Abstract

A new thiourea-based Schiff-base (L) as a fluorescent chemosensor has been designed and synthesized, which exhibits selectivity toward Hg2+ by forming a 1:2 compound based on the method of Job’s plot. The detection limit was calculated to be 6.5×10-6 mol/L. The prominent recognizable changes of L could be observed by the naked eyes and fluorescence sensing conditions. The color of the L solution changed instantly from colorless to yellow after adding Hg2+ and returned to colorless by adding I. The coordination reaction was reversible.

Supporting Info. (273KB)PDF (1.5MB)

Published online: 14th July, 2017

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-17-13724
Catalyst-Free Multicomponent Formation of Novel Acylpyrrole-Containing 6-Iminohexahydro-1H-pyrido[1,2-a]pyrimidine Derivatives

Xiaohua Wu, Zheng Zhao, Yuwei Song, and Cheng Guo*

*College of Chemistry and Molecular Engineering, Nanjing Tech University, 30 Puzhu South Road, Jiangsu, Nanjing, 211816, China

Abstract

A simple and green synthesis of acylpyrrole-containing 6-iminohexahydro-1H-pyrido[1,2-a]pyrimidine derivatives were successfully prepared via four-component reaction of 1,1-bis(methylthio)-2-nitroethene, propane-1,3-diamine, 3-(1-methyl-1H-pyrrol-2-yl)-3-oxopropanenitrile and aromatic aldehydes in ethanol under microwave irradiation. This method offers several significant advantages, including green solvent, avoidance of catalysts, high-speed reaction, outstanding selectivity, tremendous substrate diversity and no column chromatographic purification.

Supporting Info. (3MB)PDF (919KB)

Published online: 14th July, 2017

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-17-13745
Novel C2-Symmetrical Phenylboronic Acid Pinacol Esters with a Few Types of Linkers and Their Biological Activities

Makoto Furutachi, Toshiaki Gondo, Saho Goto, Saho Fuchigami, Kenta Ako, Yuki Oowada, Kazumi Yokomizo, Jian-Rong Zhou, Tomohiro Ishizaki, Takahiro Koga, Nobuhiro Kashige, Fumio Miake, and Kunihiro Sumoto*

*Faculty of Pharmaceutical Sciences, Fukuoka University, 8-19-1 Nanakuma, Jonan-ku, Fukuoka 814-0180, Japan

Abstract

We report the preparation of new C2-symmetrical cyclic phenylboronic acid derivatives and their biological activities. New targeted C2-symmetrical molecules (1) were obtained in good to excellent yields by a primitive amide bond formation reaction using the reported method starting with amino-substituted phenylboronic acid pinacol esters 2. A few C2-symmetrical phenylboronic acid ester analogues such as 5 and 7 that have two urea groups in the linker junction were also prepared in order to evaluate antibacterial and antiviral activities. The results of a structure-activity relationship study are also described.

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Published online: 13th July, 2017

Review | Regular issue | Prepress
DOI: 10.3987/REV-17-865
Development of A Glycosylation Reaction: A Key to Accessing Structurally Unique Nucleosides

Yuichi Yoshimura*

*Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan

Abstract

Nucleosides are potential drug candidates for antitumor and antiviral chemotherapies. Thus, the synthesis of structurally diverse nucleosides would contribute to the search for new antitumor and antiviral agents. The use of the glycosylation reaction to synthesize nucleoside derivatives would be a practical way to prepare nucleosides with unnatural sugar moieties. Therefore, we synthesized many nucleoside derivatives by using new glycosylation reactions categorized into three types: 1) a Pummerer-type glycosylation reaction used for constructing 4’-thionucleoside skeletons, 2) a sulfur-assisted Mitsunobu reaction used for isonucleoside syntheses, and 3) an oxidative coupling reaction catalyzed by hypervalent iodine for carbocyclic nucleosides and in the syntheses of dihydropyranonucleosides. In this review, we describe the development of the glycosylation reactions and their application to the synthesis of various structurally unique nucleoside derivatives.

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Published online: 13th July, 2017

Paper | Regular issue | Prepress
DOI: 10.3987/COM-17-13743
Synthesis of 2,3-Dihydrobenzo[b]thiophen-3-amine 1,1-Dioxide Derivatives via LDA-Mediated Cyclization of o-(Alkylsulfonyl)benzyl Azides with Denitrogenation

Kazuhiro Kobayashi,* Yuuki Chikazawa, and Takashi Nogi

*Applied Chemistry Field, Chemistry and Biotechnology Course, Department of Engineering, Graduate School of Sustainability Science, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan

Abstract

A new and efficient method for the synthesis of 2,3-dihydrobenzo[b]thiophen-3-amine 1,1-dioxide derivatives has been developed. Thus, treatment of o-(alkylsulfonyl)benzyl azides, which are readily obtainable from commercially available starting materials by easily operational sequences, with lithium diisopropylamide (LDA) in THF at –78 ˚C gives, after aqueous workup, 2,3-dihydrobenzo[b]thiophen-3-amine 1,1-dioxides. These products can be isolated in moderate to fair yields after N-protection with acylating agents.

PDF (330KB)

Published online: 13th July, 2017

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-17-13758
Secalonic Acids H and I, Two New Secondary Metabolites from the Marine-Derived Fungus Penicillium oxalicum

Li Chen, Yan-Xue Bi, Ya-Ping Li, Xin-Xin Li, Qin-Ying Liu, Min-Gang Ying, Qiu-Hong Zheng, Lin Du,* and Qi-Qing Zhang*

*Institute for Natural Products Applications and Research Technologies, Department of Chemistry and Biochemistry, University of Oklahoma, Norman, OK 73019, United States

Abstract

Two new secalonic acid derivatives, secalonic acids H and I (1 and 2), and one known compound, secalonic acid D (3), were isolated from the marine-derived fungus Penicillum oxalicum. The planar structures and relative configurations of the new compounds were elucidated by the analyses of their 1D and 2D NMR and high-resolution mass spectrometric data. The absolute configurations were established by comparison of their experimental and calculated electronic circular dichroism spectra. The in vitro cytotoxic activities of compounds 1 and 2 were evaluated against selected human cell lines.

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Published online: 12th July, 2017

Paper | Regular issue | Prepress
DOI: 10.3987/COM-17-13735
Antiviral Activities of Some New 2,4,6-Trisubstituted 1,3,5-Triazines Having Alkoxy and/or Alkylamino Groups

Nobuko Mibu, Kazumi Yokomizo, Ai Yuzuriha, Marie Otsubo, Yuna Kawaguchi, Marina Sano, Izumi Sakai, Keita Nakayama, Jian-Rong Zhou, and Kunihiro Sumoto*

*Faculty of Pharmaceutical Sciences, Fukuoka University, 8-19-1 Nanakuma, Jonan-ku, Fukuoka 814-0180, Japan

Abstract

We report the preparation of C3- and CS-symmetrical 2,4,6-trisubstituted 1,3,5-triazine derivatives having alkoxy and/or alkylamino groups and results of biological evaluation of their anti-herpes simplex virus type 1 (anti-HSV-1) activity and cytotoxic activity against Vero cells. New targeted symmetrical molecules were obtained by using a method starting with 2,4,6-trichloro-1,3,5-triazine (1). Among the synthesized compounds, CS-symmetrical tri-aliphatic alkylamino-substituted compound 6s showed high anti-HSV-1 activity (EC50 = 5.4 μM) and low cytotoxicity (CC50 > 200 μM). The results of an SAR study suggested that the presence of two hydrogen bond donor protons of sec-amine functionality in the molecule is an important structural factor for expression of potential anti-HSV-1 activities.

Supporting Info. (198KB)PDF (481KB)

Published online: 12th July, 2017

Paper | Regular issue | Prepress
DOI: 10.3987/COM-17-13754
Synthesis of Highly Substituted 5,6-Dihydrobenzo[j]phenanthridine Derivatives via Domino Reaction

Yuqin Wu, Lidong Li, Liangyun Yu, Zhang Qi, Feng Xue, and Xu Qi*

*School of Chemistry and Chemical Engineering, Yancheng Institute of Technology, Jianjun East Road No. 211, Yancheng 224051, China

Abstract

An atom-economical method for diynes with aryl halides under palladium-catalyzed conditions has been developed. Using unactivated simple diynes with aryl halides in the presence of palladium catalytic system afforded various 7,12-diphenyl-5-tosyl-5,6-dihydrobenzo[j]phenanthridine derivatives through C–C coupling and C–H bond activation in one step. This cascade reaction was initiated by an intermolecular [2 + 2 + 2] cycloaddition.

Supporting Info. (4.4MB)PDF (824KB)

Published online: 12th July, 2017

Additions and Corrections | Regular issue | Prepress
DOI: 10.3987/Erratum-COM-17-S(K)97
Correction to “Regioselective Introduction of Substituents to The Meso-Position of Pyrromethenone Derivative – Application to the Synthesis of Sterically Fixed Phytochrome Chromophore Anchored to the C15 Meso-Position”: Heterocycles, 2015, 90, 883: DOI: 10.3987/COM-14-S(K)97

Yudai Tanaka, Ryoji Iwamoto, Ryo Sakata, Takahiro Soeta, Kohei Endo, Shuhei Fujinami, Katsuhiko Inomata, and Yutaka Ukaji*

*Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma, Kanazawa, Ishikawa 920-1192, Japan

PDF (127KB)

Published online: 6th July, 2017

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-17-13704
A Cytotoxic Pyranonaphthoquinone from Cultured Lichen Mycobionts of Haematomma sp.

Yukiko Takenaka, Yoshiyuki Mizushina, Nobuo Hamada, and Takao Tanahashi*

*Kobe Pharmaceutical University, 4-19-1 Motoyamakita-machi, Higashinada-ku, Kobe 658-8558, Japan

Abstract

Spore-derived mycobionts of the lichen Haematomma sp. were cultivated on malt-yeast extract medium supplemented with 10% sucrose to produce a new pyranonaphthoquinone, 4, as well as two known compounds (-)-usnic acid (2) and 5-deoxy-7-methylbostrycoidin (3). The structure of 4 was determined by spectroscopic methods. The inhibitory activities of 3, 4, and 68 against mammalian DNA polymerases (pols) and cytotoxic effects against a HeLa human cervical cancer cell line were also evaluated. Compound 4 showed the strongest mammalian pol inhibitory activity and cytotoxicity (ID50 = 6.7 μM) among the tested compounds.

PDF (413KB)

Published online: 6th July, 2017

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-17-13763
Synthesis of Fused 1,2,3-Triazoles through Carbocation-Mediated Intramolecular [3+2] Cycloaddition of Azido-Propargyl Alcohols

Youlai Zhang, Junru Li , Mengdi Wang , Huan Zhang,* Hiroki Tanimoto, Tsumoru Morimoto, and Kiyomi Kakiuchi

*Tianjin Key Laboratory of Organic Solar Cells and Photochemical Conversion, School of Chemistry and Chemical Engineering, Tianjin University of Technology, Tianjin 300384, P.R. China

Abstract

A practical and efficient intramolecular cyclization reaction with azido-propargyl cations is described. Range of acids and activating reagents were selected to demonstrate the reaction conditions. Organic azides and propargyl cations generated by toluenesulfonic acid gave fused 1,2,3-triazoles undergo metal-free intramolecular azide–alkyne [3+2] cycloaddition reactions. Various fused triazoles were obtained within 30 min in good yields under mild reaction conditions.

Supporting Info. (1.6MB)PDF (391KB)

Published online: 5th July, 2017

Review | Regular issue | Prepress
DOI: 10.3987/REV-17-862
Update on the Reactivity of Saccharin: An Excellent Precursor for the Synthesis of Biologically Important Molecules

Rabia Akhtar, Ameer Fawad Zahoor,* Sajjad Ahmad, Syed Ali Raza Naqvi, Samreen Gul Khan, and Muhammad Suleman

*Department of Chemistry, Government College University Faisalabad, Faisalabad 38000, Pakistan

Abstract

Saccharin is a versatile starting material for the synthesis of different biologically active molecules. Its derivatives play an important role in medicinal chemistry as they act as analgesic, anti-inflammatory, antimicrobial, antirheumatic, antipyretic, anticancer and antioxidant agents. This review article describes the recent advances in the synthesis of saccharin derivatives reported from 2010 to 2017. This article critically summarizes the methodologies and pathways adopted by various research groups for the synthesis of these important molecules.

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Published online: 3rd July, 2017

Paper | Regular issue | Prepress
DOI: 10.3987/COM-17-13727
Synthesis of New Azole and Azine Systems Based on Chromeno[3,4-c]pyrrole-3,4-dione and Investigation of Their Cytotoxic Activity

Islam H. El Azab,* Mohamed R. E. Aly, and Adil A. Gobouri

*Department of Chemistry, Faculty of Science, Aswan University, Aswan 81528, Egypt

Abstract

A novel series of 9-substituted-chromeno[4',3':3,4]pyrrolo[2,1-c]- [1,2,4]triazole-6,7-diones (4), chromeno[4',3':3,4]pyrrolo[1,2-d]tetrazole-6,7- dione (5), 9-phenyl-6H- chromeno[4',3':3,4]pyrrolo[2,1-c][1,2,4]triazine-6,7(11H)-dione (8), chromeno[4',3':3,4]pyrrolo[2,1-c][1,2,4]triazole-6,7,9(10H)-trione (10), (3,5-substituted-pyrazol-1-yl)chromeno[3,4-c]pyrrole-3,4-dione (15-19) and thiazole derivatives (28-37) were synthesized using 1-hydrazinylchromeno[3,4-c]- pyrrole-3,4-dione )2( as a precursor. The newly synthesized compounds were characterized and evaluated for their cytotoxic activity.

PDF (1.3MB)

Published online: 30th June, 2017

Paper | Regular issue | Prepress
DOI: 10.3987/COM-17-13744
Synthesis of Long-Wavelength Absorbing Porphyrin m-Benzoic Acids as Molecular Tectons for Surface Studies

Alina Meindl, Aoife A. Ryan, Keith J. Flanagan, and Mathias O. Senge*

*Medicinal Chemistry, Trinity Centre for Health Sciences, Trinity College Dublin, St. James's Hospital, Dublin 8, Ireland

Abstract

Porphyrins are becoming increasingly important building blocks in material science. This is due in part to several favorable characteristics; such as strong absorption into the infrared region, tunable electronic properties and the possibility to modify and define the porphyrin core in multiple ways. Herein we report synthetic methodologies for porphyrin-based molecular tectons for surface studies. The study aims to generate porphyrins with directional anchoring groups of different length and we report a library of long-wavelength absorbing porphyrins with a special focus on organometallic coupling reactions for the introduction of benzoic acid moieties as anchor groups.

PDF (1.7MB)

Published online: 23rd June, 2017

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-17-13722
Four New Cantharidin Derivatives from the Chinese Blister Beetles, Mylabris phalerata

Yuan-Yuan Deng, Wei Zhang, Xue-Ping Lei, Dong-Mei Zhang, Jun He, Lei Wang,* and Wen-Cai Ye*

*JNU-HKUST Joint Laboratory for Neuroscience & Innovative Drug Research, Jinan University, Guangzhou 510630, China

Abstract

Four new cantharidin derivatives, cantharacidines A-D (1-4) were isolated from the Chinese blister beetles Mylabris phalerata. Their structures with absolute configurations were elucidated by means of NMR spectroscopy, single-crystal X-ray diffraction and electronic circular dichroism (ECD) spectral analyses. Compounds 1-3 are the first examples of natural cantharimide-carboxylic acid adducts. The inhibitory effects of compounds 1-4 on the viability of three cancer cell lines (HepG2, MDA-MB-231 and A549 cells) were evaluated by the MTT assay.

Supporting Info. (2.1MB)PDF (1.2MB)

Published online: 23rd June, 2017

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-17-13739
Three New Isoflavones from the Root of Pueraria lobata and their Bioactivities

Feng-Mei Zhang, Jing Li, Qi-Li Mi, Shi-Yun Tang, Ye-Kun Yang, Jian-Hua Chen, Chun-Bo Liu, Qin-Peng Shen, Zhi-Hua Liu, Guang-Yu Yang, Qiu-Fen Hu, Zhong-Tao Ding,* and Xue-Mei Li*

*School of Chemical Science and Technology, Yunnan University, Kunming 650091, China

Abstract

Three new isoflavones, 4′-hydroxy-6-methoxy-7methyl-isoflavone (1), 4′,6-dihydroxy-7-methylisoflavone (2), and 4′-hydroxy-7-hydroxymethyl-6- methoxyisoflavone (3), together with two known isoflavones (4 and 5), were isolated from the root of Pueraria lobata. Their structures were elucidated by spectroscopic methods, including extensive 1D- and 2D NMR techniques. Compounds 1-5 were evaluated for their anti-tobacco mosaic virus (anti-TMV) activities. The results showed that compounds 1 and 2 exhibited comparable anti-TMV activities with inhibition rates of 34.2 and 33.5%. The other compounds also showed potential anti-TMV activities with inhibition rates in the range of 21.8-25.6%, respectively. The cytotoxicities of compounds 1-5 against five human tumor cell lines (NB4, A549, SHSY5Y, PC3, and MCF7) were also tested. The results revealed that compounds 1-5 showed weak inhibitory activities against some tested human tumor cell lines with IC50 values in the range of 3.9-9.2 μM.

Supporting Info. (1MB)PDF (1.3MB)

Published online: 23rd June, 2017

Paper | Regular issue | Prepress
DOI: 10.3987/COM-17-13737
Arylation of Aniline and Amines by Pd-(N-Heterocyclic Carbene) Complexes

Neslihan Şahin, Serpil Demir Düşünceli, and İsmail Özdemir*

*Catalysis Research and Application Centre, Inönü University, 44280 Malatya, Turkey

Abstract

Aminoarenes constitute valuable building blocks in organic synthesis and an essential skeleton ubiquitously found in ligands, agrochemicals, and pharmaceuticals. This synopsis presents recent amination methods using nitrogen-heteroatom bonds as a powerful and versatile platform to rapidly synthesize diverse aminoarenes, with transition-metal catalyzed arene C-H amination. The Buchwald-Hartwig amination has been investigated theoretically and experimentally to examine the scope of possible bases under different reaction conditions. We report examples of the palladium NHC (N-heterocyclic carbene) catalyzed amination of aryl halides with anilines and amines in the presence of dimethoxyethane solvent and potassium tertiary-butoxide as a base.

PDF (915KB)

Published online: 20th June, 2017

Paper | Regular issue | Prepress
DOI: 10.3987/COM-17-13750
Synthesis of 17β-N-Phenylpyrazolyl Steroidal Derivatives and Their Inhibitory Effect on Cell Proliferation

Ning-Juan Fan,* Yuan-Feng Li, Qiu-Rui He, Shuang Liang, and Jiang-Jiang Tang*

*Biochemistry and Molecular Biology Research Platform, College of Life Science, Northwest A&F University, Yangling, Shaanxi 712100, China

Abstract

The synthesis of several 17β-N-phenylpyrazolyl derivatives steroid derived from progesterone are described. The Claisen condensations of ∆1, 4-pregnadien-3,20-dione (1) and 4-chloro-∆1,4-pregnadiene-3,20-dione (2) with dimethyl oxalate afforded 21-methoxalylpregna-1,4-diene-3,20-dione (3) and 4-chloro-21-methoxalylpregna-1,4-diene-3,20-dione (4), respectively. Furthermore, the reactions of 3 and 4 with substituted phenylhydrazines yielded 5'-pyrazolyl derivatives as main products, and the 5'-pyrazolyl isomers 6a-k (and 7a-k) were isolated from the crude reaction mixture (3'-pyrazolyl regioisomers as minor products). The newly synthetized compounds were evaluated in vitro by means of SRB assays for antiproliferative activity against HepG-2 (hepatoma), HeLa (cervix adenocarcinoma) and MCF-7 (breast adenocarcinoma). The preliminary results showed that compounds 6d, 6i and 7d possessed moderate antiproliferative activities.

Supporting Info. (2.6MB)PDF (798KB)

Published online: 19th June, 2017

Paper | Regular issue | Prepress
DOI: 10.3987/COM-17-13746
Synthesis of Isocoumarin Compounds, 8-Hydroxy-6-methoxy-3-Pentyl-1H-Isochromen-1-one and Fusariumin Analog Using Palladium-Catalyzed Carbonylation Trapping with O-Enolate

Masaki Asai, Yasunao Hattori, and Hidefumi Makabe*

*Department of Agriculture, Division of Food Science and Biotechnology, Graduate School of Science and Technology, Shinshu University, 8304 Minami-minowa, Kami-ina, Nagano 399-4598, Japan

Abstract

Concise synthesis of 6,8-dialkoxyisocoumarin framework was achieved using Pd-catalyzed carbonylation trapping with O-enolate. This methodology was applied to the synthesis of 8-hydroxy-6-methoxy-3-pentyl-1H-isochromen-1-one isolated from Tessmannia densiflora and fusariumin analog.

Supporting Info. (282KB)PDF (489KB)

Published online: 14th June, 2017

Paper | Regular issue | Prepress
DOI: 10.3987/COM-17-13736
Reaction of Electron-Deficient 3-Acetyl-1-arylpent-2-ene-1,4-diones as a Building Block of Heterocycles

Shun Kawabata, Akihiro Oishi, and Hiroshi Nishino*

*Department of Chemistry, Graduate School of Science and Technology, Kumamoto University, Kurokami 2-39-1, Chûou-Ku, Kumamoto 860-8555, Japan

Abstract

The BF3-assisted reaction of 3-acetyl-1-arylpent-2-ene-1,4-diones 1a-c with cyclohexanones and piperidin-4-ones 2a-i gave unique 3a,6a-dihydrospirofuro[2,3-d][1,3]dioxoles 3 in good to high yields. A similar reaction with the 2,3-dihydroquinolin-4(1H)-ones did not occur, but the reaction with 4-hydroxychromenone 5 mainly produced 3-furfuryl-4-hydroxychromenone 6 along with furochromenone 7. The reaction of the electron-deficient pentenedione 1a as a Michael acceptor with indole, pyrrole, furan, and N-methylaniline produced the corresponding 1,4-adducts. Especially, the indole adduct was easily converted by the Paal-Knorr synthesis into the corresponding furanyl-, pyrrolyl-, and thiophenyl-substituted indoles. The reaction details and the structure determination of the products are described.

PDF (888KB)

Published online: 13th June, 2017

Paper | Regular issue | Prepress
DOI: 10.3987/COM-17-13720
Synthesis of 7,8-Dihydropyrido[2,3-d]pyrimidine Derivatives from 4,6-Dichloro-2-(methylsulfanyl)pyrimidine

Kazuhiro Kobayashi,* Ippei Nozawa, Takuma Ueyama, Hiroaki Utsumi, Hidetaka Hiyoshi, and Kazuto Umezu

*Applied Chemistry Field, Chemistry and Biotechnology Course, Department of Engineering, Graduate School of Sustainability Science, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan

Abstract

A new and convenient method for the preparation of 7,8-dihydropyrido[2,3-d]pyrimidine derivatives has been developed utilizing a three-step sequence starting with a commercially available 4,6-dichloro-2-(methylsulfanyl)pyrimidine (DCSMP). Thus, successive treatment of the starting material with LDA and cinnamaldehyde or its derivatives leads to the formation of 3-aryl-1-[4,6-dichloro-2-(methylsulfanyl)pyrimidin-5-yl]prop-2-en-1-ols. After replacement of one of the two chloro-substituents with primary amines, cyclization of the resulting precursors gives the desired products on treatment with methanesulfonyl chloride in the presence of triethylamine.

PDF (247KB)

Published online: 9th June, 2017

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-17-13690
One-Pot Four Component Reaction for the Synthesis of 1-(1H-Indol-2-yl)-1H-pyrazolo[1,2-b]phthalazine-5,10-dione Derivatives by Self-Catalysis

Faruq Mohammad* and Hamad A. Al-Lohedan

*Surfactant Research Chair, Department of Chemistry, King Saud University, P.O. Box 2455, Riyadh-11454, Saudi Arabia

Abstract

In this, we performed a four component domino reaction of phthaloyl dichloride, hydrazine hydrate, indole-3-carboxaldehydes and malononitrile/ethyl cyanoacetate to form 1-(1H-indol-2-yl)-1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives by in situ generation of HCl as catalyst in refluxing ethanol for 1 h in good yields. This four component domino reaction transformation presumably proceeds via addition/dehydrohalogenation/condensation/cyclization of reactions. The material was thoroughly characterized at various stages of its formation by means of FTIR, NMR spectroscopic and Mass spectrometric analysis and is confirmed to be the derivative of 1-(1H-indol-2-yl)-1H-pyrazolo[1,2-b]phthalazine-5,10-dione.

Supporting Info. (1.4MB)PDF (855KB)

Published online: 9th June, 2017

Paper | Regular issue | Prepress
DOI: 10.3987/COM-17-13726
Ultrasound-Mediated Three-Component Reaction “On-Water” Protocol For the Synthesis of Novel Mono- and bis-1,3-Thiazin-4-one Derivatives

Wael A. A. Arafa,* Ashraf M. Mohamed, and Ahmed F. Abdel-Magied

*Department Of Chemistry, Fayoum University, Fayoum 12975, Egypt

Abstract

Green synthetic and catalyst-free strategy towards the synthesis of novel mono- and bis-1,3-thiazin-4-one scaffolds through a one pot, reaction of carbon disulfide, monoacetylenic esters and amines under ultrasonication has been reported. The merits of this protocol comprise no need for tedious workup steps and afforded the desired products in excellent yields make this synthetic protocol more efficient and worthy of further attentiveness. Moreover, the method exhibited excellent score in a number of green metrics.

PDF (1.1MB)
24 data found. 1 - 24 listed