Regular & Special Issues

20 data found. 1 - 20 listed

Published online: 8th October, 2015

Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13310
Expedient Synthesis of Novel Glycosyl Thiazole Derivatives

Feng-chang Cheng, Long Yin, Wei-wei Liu,* Qu-xiang Li, Li-juan Tang, Da-hua Shi, and Zhi-ling Cao

*School of Chemical Engineering, Huaihai Institute of Technology, Lianyungang City, Jiangsu Province 222005, China


An efficient protocol for the synthesis of novel glycosyl thiazole derivatives starting from the commercially available D-glucosamine hydrochloride was described by reaction of 1-(1,3,4,6-tetra-O-benzyl-2-deoxy-β-D-glucopyranos-2-yl)thiourea 8 with each of substituted α-bromoacetophenone in ethanol. 1-(1,3,4,6-Tetra-O-benzyl-2-deoxy-β-D-glucopyranos-2-yl)thiourea was an important intermediate, and its synthetic methods were discussed by comparing two different synthetic routes. Moreover, 2-isothiocyanate-1,3,4,6-tetra-O-benzyl-2-deoxy-β-D-glucopyranose was obtained in a new and convenient way. Finally, a series of novel glycosyl incorporated with thiazole moiety was synthesized in good purities and overall yields.

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Published online: 7th October, 2015

Short Paper | Special issue | Prepress
DOI: 10.3987/COM-15-S(T)23
Dilithiation of A 2,1-Benzothiazine

Nathan L. Calkins, Carissa S. Hampton, and Michael Harmata*

*Room 125, Department of Chemistry, University of Missouri-Columbia, 601 South College Avenue, Columbia, Missouri 65211, U.S.A.


Treatment of benzothiazine 24 with excess amounts of n-BuLi followed by trapping with selected electrophiles afforded products that suggested the formation of dilithio species. Interestingly, however, the scope of the electrophilic trapping was rather limited, electrophilic sources of halogens and disulfides functioning nearly uniquely and competent electrophilic trapping agents in the process.

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Published online: 6th October, 2015

Paper | Special issue | Prepress
DOI: 10.3987/COM-15-S(T)8
New Applications of Hetaryl Thioketones for the Synthesis of Hetaryl-substituted Ethenes via ‘Two-fold Extrusion Reaction’

Grzegorz Mlostoń, Katarzyna Urbaniak, Aneta Pawlak, and Heinz Heimgartner*

*Institute of Organic Chemistry, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland


A series of aryl/hetaryl thioketones was applied for the reactions with aryl/hetaryldiazomethanes yielding, after elimination of N2, the corresponding thiiranes. The relatively unstable dihetaryldiazomethanes were generated in situ from the corresponding hydrazones by oxidation with DMSO. The obtained thiiranes were converted into tetraaryl/hetaryl-substituted ethenes in good yields by desulfurization performed with tris(diethylamino)phosphane.

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Published online: 6th October, 2015

Paper | Special issue | Prepress
DOI: 10.3987/COM-15-S(T)7
Access to Apoerysopine and Pratosine Skeletons via Intramolecular Carbolithiation and Palladium-Catalyzed Alkenylation Reactions

Estíbaliz Coya, Esther Lete, and Nuria Sotomayor*

*Departamento de Química Orgánica, Facultad de Ciencia y Tecnologia, Universidad del País Vasco, Barrio Sarriena s/n. Leioa (Bizkaia) Bilbao 48940, Spain


Pyrrolo[1,2-a]benzazepinyl acetamides, obtained through carbolithiation reactions, have been used as intermediates in the access to Apoerysopine skeleton. Derivatization implies reduction to the correponding aldehyde using the Snieckus procedure for in situ generation of the Schwartz reagent, followed by Wittig reaction and intramolecular Pd(II)-catalyzed C-H alkenylation. The same sequence has been applied for the obtention of Pratosine from a pyrroloisoquinoline intermediate.

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Published online: 6th October, 2015

Paper | Special issue | Prepress
DOI: 10.3987/COM-15-S(T)14
New Gas-Phase Domino Processes Leading to Benzopyranones and Benzofurans

R. Alan Aitken* and Da Chang

*School of Chemistry, University of St. Andrews, North Haugh, St Andrews, Fife KY 16 9ST, U.K.


A new domino approach to flavones by gas phase pyrolysis of β,γ-dioxophosphonium ylides containing a 2-methoxyphenyl group is frustrated by unexpected and novel decarbonylation of the intermediate flavon-3-yl radical leading to 2-phenylbenzofuran. Alternative approaches based on dioxolane protection of one carbonyl, or selective elimination in β,β'-dioxo or β-oxo-β'-thioxo ylides were not successful, but pyrolysis of a β-oxo-β'-phenylimino ylide did give the required domino reaction leading to a protected benzopyranone in moderate yield.

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Published online: 5th October, 2015

Review | Regular issue | Prepress
DOI: 10.3987/REV-15-824
Ring Opening Ring Closure Reactions with 3-Substituted Chromones under Nucleophilic Conditions

Magdy A. Ibrahim,* Nasser M. El-Gohary, and Sara Said

*Department of Chemistry, Faculty of Education, Ain Shams University, Roxy, Cairo 11711, Egypt


This review covers the ring opening ring closure (RORC) reactions of 3-substituted chromones with a variety of nitrogen and carbon nucleophiles. The nucleophilic reagent usually attack 3-substituted chromones at the C-2 position with γ-pyrone ring opening followed by further transformation during the course of the reaction producing a variety of products depending on the substrate at position 3, the nature of nucleophile and the reaction conditions.

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Published online: 30th September, 2015

Additions and Corrections | Regular issue | Prepress
DOI: 10.3987/Erratum-COM-15-13194
Errata “Preparation and Antibacterial Evaluation of Some Symmetrical Twin-Drug Type Bivalent Molecules”: HETEROCYCLES, 2015, 91, 1676, DOI: 10.3987/COM-15-13263

Fumiko Fujisaki, Makoto Furutachi, Ryou Fujiwara, Miriko Okabe, Hatsumi Aki, Nobuhiro Kashige, Fumio Miake, and Kunihiro Sumoto*

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

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Published online: 29th September, 2015

Short Paper | Special issue | Prepress
DOI: 10.3987/COM-15-S(T)34
Construction of cis-Fused Hydrindane Skeleton with A Lactone Tether Utilizing Intramolecular Diels-alder Reaction

Shuqiang Yin, Kenji Takai, Daishiro Minato, Kenji Sugimoto, Hideki Ohtsu, Kiyoshi Tsuge, and Yuji Matsuya*

*Graduate School of Medicine and Pharmaceutical Sciences for Research, University of Toyama, Sugitani 2630, Toyama, 930-0194, Japan


Synthetically important, cis-fused hydrindane skeleton having quaternary angular stereogenic centers was selectively furnished by intramolecular Diels-Alder reaction of ester-tethered precursor via endo transition state. The reaction was applicable for a construction of the steroidal BCD ring system with cis-hydrindane framework.

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Published online: 24th September, 2015

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13265
Efficient Microwave-assisted Syntheses of A Series of Novel Mono(imino)pyrrolyl Compounds

Biyun Su,* Xiaoteng Li, Xudong Wang, and Qianding Li

*College of Chemistry and Chemical Engineering, Xi’an Shiyou University, 18, 2nd Dianzi Road, Xi’an, Shanxi 710065, China


A series of novel mono(imino)pyrroles that were hard to prepare under traditional solvent reaction condition were readily synthesized under solvent free condition using microwave chemistry via p-TSA (p-toluenesulfonic acid) catalyzed Schiff base condensation. The structures of the compounds were characterized by means of MS, 1H NMR, IR, elementary analysis and X-ray diffraction analysis. The reactivity of different aromatic amines with 2-acetylpyrrole was discussed.

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Published online: 24th September, 2015

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13277
Nano-Copper Catalyzed Three-Component Tandem Cycloaddition and N-Alkylation Reaction from Aminophenylacetylenes, Sodium Azide and Alkyl Halides

Fangli Gang, Taosheng Dong, Guangli Xu, Ying Fu, and Zhengyin Du*

*College of Chemistry and Chemical Engineering, Northwest Normal University, Anning East Road, 967, 730070, China


Nano-copper catalyzed one-pot three-component method is realized from aminophenylacetylenes, sodium azide and alkyl halides via tandem 3+2 dipolar cycloaddition reaction and N-alkylation reaction. This synthetic process gave the product of 1-alkyl-4-(N-alkylaminophenyl)-1,2,3-triazoles in good yields.

Supporting Info. (4.5MB)PDF (943KB)

Published online: 24th September, 2015

Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13281
Synthesis, Antimicrobial and Antihuman Liver Cancer Activities of Novel Sulfonamides Incorporating Benzofuran, Pyrazole, Pyrimidine, 1,4-Diazepine and Pyridine Moieties were Prepared from (E)-4-(3-(Dimethylamino)acryloyl)-N-ethyl-N-methylbenzenesulfonamide

Sami A. Al-Harbi and Mahmoud S. Bashandy*

*Department of Chemistry, Al-Azhar University, Nasr City, Cairo 002, Egypt


Reaction of compound 1 with dimethylformamide dimethylacetal gave enaminone 2, which reacts with 1,4-benzoquinone and 4-amino-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one to afford 6 and 7, respectively. Treatment of 2 with hydroxylamine hydrochloride gave cyanoacetyl derivative 14. Enaminone 2 reacts with guanidine hydrochloride and phenylhydrazine to furnish 2-aminopyrimidine and pyrazole derivatives 15 and 16, respectively. Enaminone 2 also reacts with ethylenediamine and acetylacetone to afford the corresponding derivatives of 1,4-diazepine 18 and pyridine 20, respectively. The structures of the newly synthesized compounds were confirmed by elemental analysis, IR, 1H NMR, 13C NMR and Ms spectral data. All the synthesized compounds were evaluated for antimicrobial activity. Compounds 6 and 20 were found to be highly active against the all microorganisms. In addition, all the compounds were tested in-vitro antihuman liver hepatocellular carcinoma cell line (HepG2). Compounds 14, 6, 18 and 16 with selectivity index (SI) values of 70.92, 55.56, 29.56 and 15.00, respectively, exhibited better activity than methotrexate (MTX) as a reference drug with SI value of 13.30. Virtual screening using molecular docking studies of the synthesized compounds was performed by Molecular Operating Environment (MOE). The results indicated that some synthesized compounds suitable inhibitor against dihydrofolate reductase (DHFR) enzyme (PDB ID: 4DFR) with further modification.

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Published online: 24th September, 2015

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13291
An Efficient Synthesis of Novel Dispiro Derivatives via Three-Component 1,3-Dipolar Cycloaddition Reactions under Ultrasound Irradiation

Chunling Shi* and Jun Zhou

*School of Chemistry and Chemical Engineering, Xuzhou Institute of Technology, Xuzhou City New Urban Area Lishui Road, 221111, China


A series of new dispiro compounds were synthesized via the three-component 1,3-dipolar cycloaddition reaction of acenaphthenequinone, thiazolidine-4-carboxylic acid and (Z)-5-benzylidene-2-thioxothiazolidin-4-one or (Z)-5-benzylidenethiazolidine-2,4-dione in ethanol under ultrasound irradiation. This protocol has the advantages of mild reaction conditions, high yields and short reaction time.

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Published online: 24th September, 2015

Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13300
Four New Compounds from Pouzolzia zeylanica (L.) Benn. var. Microphylla

Chu-Qian Zhong, Shu-Hong Tao, Zhi-Bo Yi, Li-Bing Guo,* Yu-Feng Xie, and Yan-Fen Chen

*School of Traditional Chinese Medicine, Guangdong Pharmacutical University, University City, Waihuan Road 280#, Guangzhou, Guangdong, 510006, China


Two new stilbenes, pouzolignan D (1) and K (2), and two new norlignans, pouzolignan L (3) and M (4), together with four known flavonoids, rhamnocitrin (5), rhamnetin (6), isorhamnetin (7) and quercetin(8), were isolated from the aerial parts of Pouzolzia zeylanica (L.) Benn. var. microphylla (Wedd.) W. T. Wang. Their structures were elucidated by spectroscopic methods, including UV, IR, HR-ESI-TOF-MS, 1D and 2D NMR experiments.

Supporting Info. (2.4MB)PDF (1.1MB)

Published online: 17th September, 2015

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-15-13301
Chromones from the Twigs of Cassia fistula and Their Anti-Tobacco Mosaic Virus Activities

Qiu-Fen Hu, Li-Mei Li, Dong-Lai Zhu, Zhen-Hua Yu, Jian-Bo Zhan, Jie Lou, Ye-De Wang, Kun Zhou, Min Zhou, Yin-Ke Li, and Xue-Mei Gao*

*Key Laboratory of Ethnic Medicine Resource Chemistry, State Ethnic Affairs Commission & Ministry of Education, School of Chemistry and Biotechnology, Yunnan University of Nationalities, Kunming, Jingming South Road, Chenggong New District, Kunming, Yunnan 650500, China


Three new chromones, 2-(3-hydroxypropanoyl)-8-methoxy-5-(2-oxopropyl)-4H-chromen-4-one (1), 8-hydroxy-2-(3-hydroxypropanoyl)-5-(2-oxopropyl)-4H-chromen-4-one (2), 2-(2-hydroxyethyl)-7-methoxy-5-(2-oxopropyl)-4H-chromen-4-one (3), together with four known chromones (3-7) were isolated from the twigs of Cassia fistula. Their structures were determined by means of HRESIMS and extensive 1D and 2D NMR spectroscopic studies. Compounds 1-3 were tested for their anti-tobacco mosaic virus (anti-TMV) activities. The results revealed that compound 1-3 showed high anti-TMV activities with inhibition rates of 26.6, 28.2 and 29.7%, respectively. These rates are close to that of positive control.

Supporting Info. (205KB)PDF (1.2MB)

Published online: 2nd September, 2015

Paper | Special issue | Prepress
DOI: 10.3987/COM-15-S(T)6
Practical and Facile Route to A Functional Intermadiate from Stigmasterol for The Synthesis of 1α-Hydroxyvitamin D5 and Related Compounds

Michiyasu Takahashi, Seiya Hosokawa, Yuuya Ono, and Noboru Kubodera*

*International Institute of Active Vitamin D Analogs, 35-6, Sankeidai, Mishima, Shizuoka 411-0017, Japan


As a functional and versatile intermediate for the synthesis of 1α-hydroxyvitamin D5 and related compounds, 1α,2α-epoxy-3β-hydroxystigmasta- 5,7-diene was synthesized by a practical and facile 17-step route from stigmasterol in 17% overall yield.

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Published online: 24th August, 2015

Paper | Special issue | Prepress
DOI: 10.3987/COM-15-S(T)5
Total Synthesis of Carbazole-1,4-quinone Alkaloid Koeniginequinones A and B based on a One-Pot Cyclocarbonylation Procedure from 2-Alkenyl-3-iodoiodoindole

Takashi Nishiyama, Nanase Satsuki, Satoshi Hibino,* Mami Fujii, Takumi Abe, Minoru Ishikura, and Tominari Choshi*

*Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University, Fukuyama, Hiroshima 729-0292, Japan


Total syntheses of koeniginequinones A and B, isolated from Murraya koenigii, were newly achieved by constructing of carbazole-1,4-quinone using a one-pot Pd-catalyzed cyclocarbonylation method with 2-(but-2-en-1-yl)-3-iodoindoles derived from known methyl 6-methoxyindole-2-carboxylate and methyl 5,6-dimethoxyindole-2-carboxylate, followed by desilylation, and an oxidation sequence.

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Published online: 5th August, 2015

Short Paper | Special issue | Prepress
DOI: 10.3987/COM-15-S(T)4
Synthesis of Benzophenone and Phenylazide Derivatives of Salicin for Functional Analysis of the Bitter Taste Receptor Using Photoaffinity Labeling

Takuma Yoshida, Yasuyuki Hashidoko, and Makoto Hashimoto*

*Division of Applied Science, Graduate School of Agriculture, Hokkaido University, Kita 9 Nishi 9, Kita-ku, Sapporo, Hokkaido 060-8589, Japan


Salicin is a substance that is well known for its bitter taste. Photoreactive benzophenone and phenylazide derivatives of salicin are for the functional analysis of interactions between the bitter taste receptor and salicin. First synthesis of these derivatives was prepared from acetobromo-α-D-glucose via glucosidation with salicylaldehyde derivatives followed by reduction of aldehyde to form salicin skeleton.

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Published online: 24th July, 2015

Paper | Special issue | Prepress
DOI: 10.3987/COM-15-S(T)3
Synthesis of 2-Arylquinoxalines: Triarylstibane-Catalyzed Oxidative Cyclization of α-Hydroxy Ketones with 1,2-Diamines Under Aerobic Conditions

Mio Matsumura, Rie Takada, Yuu Ukai, Mizuki Yamada, Yuki Murata, Naoki Kakusawa, and Shuji Yasuike*

*Faculty of Pharmaceutical Sciences, Aichi Gakuin University, 1-100 Kusumoto-cho Chikusa-ku Nagoya city 464-8650, Japan


The reaction of -hydroxy ketones with 1,2-diamines in the presence of triphenylstibane (10 mol%) as catalyst led to the formation of 2-arylquinoxalines in moderate to good yield under aerobic conditions. This reaction is the first example of oxidative cyclization catalyzed by organoantimony compounds.

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Published online: 15th July, 2015

Paper | Special issue | Prepress
DOI: 10.3987/COM-15-S(T)2
Synthesis of 3,4-Dihydro-2H-1,3-benzoxazine-2-thiones via Cyclization of 2-(1-Isothiocyanatoalkyl)phenols

Kazuhiro Kobayashi,* Hiroki Inouchi, Naoki Matsumoto, and Yuuki Chikazawa

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


Convenient sequences for the preparation of 3,4-dihydro-2H-1,3-benzoxazine-2-thiones from 2-hydroxybenzaldehyde and 2-hydroxyphenyl ketones or 2-methylphenols have been developed, which both employ cyclization of 2-(1-isothiocyanatoalkyl)phenols generated in situ under mild conditions.

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Published online: 10th June, 2015

Short Paper | Special issue | Prepress
DOI: 10.3987/COM-15-S(T)1
Crystal Structures of N,N’-bis(5-Dodecyloxytropon-2-yl)piperazine and N,N’-bis(4-Butoxyphenyl)piperazine

Kanji Kubo,* Emi Yamamoto, Taisuke Matsumoto, Seiji Ujiie, and Akira Mori

*Department of Life Science and Technology, Faculty of Engineering, Hokkai-Gakuen Univiersity, Sapporo, Hokkaido 062-8605, Japan


The crystal structures of N,N’-bis(5-dodecyloxytropon-2-yl)piperazine (1) and N,N’-bis(4-butoxyphenyl)piperazine (2) were analyzed by X-ray crystallography. The molecules of 1 and 2 sits on a center of symmetry such that the two aromatic rings are in an anti conformation with respect to one another across the piperazine ring. The molecules (1, 2) forms a tilted layer structure via intermolecular C-H∙∙∙O and C-H∙∙∙π interactions in 1 and intermolecular C-H∙∙∙O, C-H∙∙∙N, and C-H∙∙∙π interactions in 2.

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20 data found. 1 - 20 listed