A Three-Component Approach to 3,5-Diaryl-1,2,4-thiadiazoles under Transition-Metal-Free Conditions

被引：102

作者：

Xie, Hao ^{[1
]}

Cai, Jinhui ^{[1
]}

Wang, Zilong ^{[1
]}

Huang, Huawen ^{[1
]}

Deng, Guo-Jun ^{[1
]}

机构：

[1] Xiangtan Univ, Coll Chem, Minist Educ, Key Lab Environm Friendly Chem & Applicat, Xiangtan 411105, Peoples R China

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 09期

基金：

中国国家自然科学基金;

关键词：

VITRO ANTITUBERCULOSIS ACTIVITY; OXIDATIVE DIMERIZATION; 3,5-DISUBSTITUTED 1,2,4-THIADIAZOLES; GASTRIC (H+/K+)-ATPASE; REVERSIBLE INHIBITORS; COUPLING REACTIONS; ELEMENTAL SULFUR; DERIVATIVES; DESIGN; AGENTS;

D O I：

10.1021/acs.orglett.6b00806

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel route is disclosed for the synthesis of 1,2,4-thiadiazoles starting from amidines, elemental sulfur, and 2-methylquinolines or aldehydes under transition-metal-free conditions. This three-component approach affords efficient and rapid access to 3,5-diaryl substituted 1,2,4-thiadiazoles with good tolerance of a broad range of funcitional groups. Mechanistic studies reveal a radical-involved pathway.

引用

页码：2196 / 2199

页数：4

共 45 条

[1] Synthesis, characterization and antimicrobial activity evaluation of new 2,4-Thiazolidinediones bearing imidazo[2,1-b][1,3,4]thiadiazole moiety [J].

Alagawadi, Kallanagouda R. ;

Alegaon, Shankar G. .

ARABIAN JOURNAL OF CHEMISTRY, 2011, 4 (04) :465-472

[2] Synthesis and antimicrobial evaluation of some fused heterocyclic [1,2,4]triazolo [3,4-b][1,3,4]thiadiazole derivatives [J].

Almajan, Gabriela Laura ;

Barbuceanu, Stefania-Felicia ;

Bancescu, Gabriela ;

Saramet, Ioana ;

Saramet, Gabriel ;

Draghici, Constantin .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (12) :6139-6146

[3] Multi-component coupling reactions:: synthesis of a guanidine containing analog of the hexahydropyrrolo[3,2-c] quinoline alkaloid martinelline [J].

Batey, RA ;

Powell, DA .

CHEMICAL COMMUNICATIONS, 2001, (22) :2362-2363

[4] HIGHLY EFFICIENT SYNTHESIS OF 3,5-DIARYL-1,2,4-THIADIAZOLES IN WATER-WET PASTE CONDITIONS [J].

Boeini, Hassan Zali .

SYNTHETIC COMMUNICATIONS, 2011, 41 (19) :2932-2938

[5] REVERSIBLE INHIBITORS OF THE GASTRIC (H+/K+)-ATPASE .1. 1-ARYL-4-METHYLPYRROLO[3,2-C]QUINOLINES AS CONFORMATIONALLY RESTRAINED ANALOGS OF 4-(ARYLAMINO)QUINOLINES [J].

BROWN, TH ;

IFE, RJ ;

KEELING, DJ ;

LAING, SM ;

LEACH, CA ;

PARSONS, ME ;

PRICE, CA ;

REAVILL, DR ;

WIGGALL, KJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (02) :527-533

[6] OXIDATION AND OTHER REACTIONS OF THIOBENZAMIDE DERIVATIVES OF RELEVANCE TO THEIR HEPATOTOXICITY [J].

CASHMAN, JR ;

HANZLIK, RP .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (24) :4645-4650

[7] Advances in the synthesis and recent therapeutic applications of 1,2,4-thiadiazole heterocycles [J].

Castro, A ;

Castaño, T ;

Encinas, A ;

Porcal, W ;

Gil, C .

BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (05) :1644-1652

[8] Four-Component Approach to N-Substituted Phenothiazines under Transition-Metal-Free Conditions [J].

Chen, Jinjin ;

Li, Guozheng ;

Xie, Yanjun ;

Liao, Yunfeng ;

Xiao, Fuhong ;

Deng, Guo-Jun .

ORGANIC LETTERS, 2015, 17 (23) :5870-5873

[9] Hypervalent iodine in synthesis. 84. Facile synthesis of 3,5-disubstituted 1,2,4-thiadiazoles by oxidative dimerization of thioamides using polymer-supported iodobenzene diacetate [J].

Cheng, DP ;

Chen, ZC .

SYNTHETIC COMMUNICATIONS, 2002, 32 (14) :2155-2159

[10] THE REACTION OF NITROUS ACID WITH THIOBENZAMIDES [J].

CRONYN, MW ;

NAKAGAWA, TW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (14) :3693-3693

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