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8 data found. 1 - 8 listed

Published online: 18th October, 2018

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-18-13986
Synthesis of 4-Arylisoquinoline-1(2H)-thione Derivatives by Sodium Hydride-Mediated Cyclizations of 2-(1-Arylethenyl)benzothioamides

Kazuhiro Kobayashi* and Takuma Ueyama

*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 facile method for the general preparation of isoquinoline-1(2H)-thione derivatives has been developed. Thus, the sodium hydride-mediated cyclization of N-substituted 2-(1-arylethenyl)benzothioamides, which are derived from the reaction of 2-(1-arylethenyl)phenyllithiums with isothiocyanates, gives 2-substituted 4-aryl-3,4-dihydroisoquinoline-1(2H)-thiones. In addition, the use of N-substituted 2-(1-aryl-2-methoxyethenyl)benzothioamides from 2-(1-aryl-2-methoxyethenyl)phenyllithiums and isothiocyanates affording 2-substituted 4-arylisoquinoline-1(2H)-thiones is described.

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Published online: 15th October, 2018

Review | Regular issue | Prepress
DOI: 10.3987/REV-18-892
The Dawn, Evolution and Personal Reminiscences in Studies of Glycosyl Isocyanates and Isocyanides

Yoshiyasu Ichikawa*

*Faculty of Science, Kochi University, 2-5-1, Akebono-cho, Kochi 780-8520, Japan

Abstract

Historical background and personal reflections on my research career studying glycosyl isocyanates and isocyanides are described

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Published online: 10th October, 2018

Paper | Regular issue | Prepress
DOI: 10.3987/COM-18-13967
A New HBT-based Fluorescent Probe for Hydrazine Detection in Aqueous Solution

Jing-Hua Dong,* Jia Deng, and Yuan Zhang

*Hubei Key Laboratory of Pollutant Analysis & Reuse Technology, College of Chemistry and Chemical Engineering, Hubei Normal University, 11, Cihu Road, Huangshi, Hubei Province 435002, China

Abstract

A new HBT-based fluorescent probe is designed and synthesized for the detection of hydrazine based on Gabriel-type hydrazinolysis reaction mechanism. The probe responds selectively to hydrazine with obvious turn-on fluorescence. The water sample analysis indicated its great potential in the environment monitoring of hydrazine in aqueous solution.

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Published online: 10th October, 2018

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-18-13972
Vanadium-Catalyzed Achmatowicz and Aza-Achmatowicz Rearrangement Reactions

Wang-Ze Song,* Nan Zheng, Ming Li, Karim Ullah, Jun-Hao Li, Kun Dong, and Yu-Bin Zheng

*School of Pharmaceutical Science and Technology, Dalian University of Technology, No.2 Linggong Road, Ganjingzi District, Dalian City, Liaoning Province 116024, China

Abstract

A novel and efficient synthesis of substituted pyranones and pyridinones is developed using cumene hydroperoxide as oxidant by vanadium-catalyzed Achmatowicz rearrangement and aza-Achmatowicz rearrangement reactions. It offers a sustainable and environmentally benign approach to access multisubstituted pyranones or pyridinones derivatives.

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Published online: 28th September, 2018

Paper | Regular issue | Prepress
DOI: 10.3987/COM-18-13968
One-Pot Synthesis of Isoindolin-1-ones from Nitroarenes and o-Phthalaldehyde via Indium-Mediated Reductive Condensation Reactions

Eungyung Kim, Mingyeong Jeong, Byung Min Lee, and Byeong Hyo Kim*

*Department of Chemistry, Kwangwoon University, 447-1, Wolgye-Dong Nowon-ku, Seoul, 139-701, Korea

Abstract

Indium-mediated reductive condensation reactions of various nitroarenes with o-phthalaldehyde toward isoindolin-1-ones were investigated. In the presence of indium/AcOH in toluene at reflux, nitroarenes were coupled and cyclized with o-phthalaldehyde to produce corresponding isoindolin-1-ones with reasonable yields.

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Published online: 26th September, 2018

Short Paper | Regular issue | Prepress
DOI: 10.3987/COM-18-13966
One-Pot Synthesis of 3-Oxo-2H,4H-1,4-benzothiazine-2-carbonitrile Derivatives via Cyclization of Methyl {[2-(Cyanomethyl)sulfanyl]phenyl}carbamate

Kazuhiro Kobayashi,* Kazuki Kawano, and Daiki Fujiwara

*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 facile method for the synthesis of 3-oxo-2H,4H-1,4-benzothiazine-2-carbonitrile (2-cyano-2H-1,4-benzothiazin-3(4H)-one) derivatives has been developed. Sodium hydride-mediated cyclization of methyl {[2-(cyanomethyl)sulfanyl]phenyl}carbamate, which can be easily prepared from commercially available 2-aminobenzenethiol in two steps, allows the synthesis of 3-oxo-2H,4H-1,4-benzothiazine-2-carbonitrile and its 2-mono- and 2,4-di- alkylated derivatives in one-pot.

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Published online: 19th September, 2018

Review | Regular issue | Prepress
DOI: 10.3987/REV-18-893
Synthesis, Reaction and Biological Activity of Pyrazolo[5,1-c][1,2,4]benzotriazine 5-Oxides

Ghodsi Mohammadi Ziarani,* Manizheh Mostofi, Negar Lashgari,* and Mohammad Mahdavi

*Department of Chemistry, Alzahra University, Tehran, Iran

Abstract

[1,2,4]Benzotriazine fused to pyrazole ring is a privileged heterocyclic scaffold present in numerous pharmacologically active compounds. Till date, various pyrazolo[5,1-c][1,2,4]benzotriazine 5-oxides and their deoxy analogues, possessing a broad spectrum of potent pharmacological activities, have been reported. In this review, we highlighted synthesis, chemical reactions, medicinal chemistry aspects and applications of fused pyrazole derivatives of [1,2,4]benzotriazine analogues reported so far.

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Published online: 5th September, 2018

Review | Regular issue | Prepress
DOI: 10.3987/REV-18-894
Tetrazole-Fragmentation for the Generation of Alkylidene Carbenes from Cyanophosphates under Neutral Conditions and Its Application to Organic Synthesis

Hiroki Yoneyama and Shinya Harusawa*

*Laboratory of Pharmaceutical Organic Chemistry, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan

Abstract

The generation of alkylidene carbenes through tetrazole-fragmentation from cyanophosphates (CPs) under neutral conditions and its application to organic synthesis are reviewed. The following topics are covered: 1) The formation of α-azidotetrazoles and their transformation into alkynes under microwave heating conditions, 2) the transformation of carbonyl compounds into homologous alkynes via CPs, 3) the synthesis of five-membered unsaturated cyclic compounds from ketones via CPs, 4) the synthesis of C4-linked Cn-triazole ribonucleoside phosphoramidites from β-ribofuranosyl-Cn-acetylenes, and 5) the synthesis of (_)-neplanocin A and one of its important synthetic intermediates using cyclopentene-formation from CPs.

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8 data found. 1 - 8 listed