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通过格罗布克-布莱克本-比纳梅反应/亲核芳环取代反应/环链叠氮互变异构化策略实现无溶剂和无催化剂的一锅法绿色键连型稠合双杂环合成。

Solvent- and Catalyst-Free One-Pot Green Bound-Type Fused Bis-Heterocycles Synthesis via Groebke-Blackburn-Bienaymé Reaction/SAr/Ring-Chain Azido-Tautomerization Strategy.

作者信息

Claudio-Catalán Miguel Ángel, Pharande Shrikant G, Quezada-Soto Andrea, Kishore Kranthi G, Rentería-Gómez Angel, Padilla-Vaca Felipe, Gámez-Montaño Rocío

机构信息

Departamento de Química, División de Ciencias Naturales y Exactas and Departamento de Biología, División de Ciencias Naturales y Exactas, Universidad de Guanajuato, Noria Alta S/N, Col. Noria Alta, Guanajuato, C.P. 36050 Guanajuato, México.

出版信息

ACS Omega. 2018 May 31;3(5):5177-5186. doi: 10.1021/acsomega.8b00170. Epub 2018 May 14.

Abstract

A new, efficient, green, endogenous water-triggered, solvent- and catalyst-free ultrasound-assisted one-pot Groebke-Blackburn-Bienaymé reaction/SAr/ring-chain azido-tautomerization strategy to synthesize bound-type fused bis-heterocycles imidazo or benzo[]imidazo[2,1-]thiazoles and 1,5-disubstituted tetrazole (1,5-DsT) containing quinoline moiety is described, which allows synthesis of two types of fused heterocycles in one step under mild green conditions. Antibacterial and antiamebic activities of selected newly synthesized compounds were carried out against three bacterial species: Gram-positive bacterium ATCC 6538 and Gram-negative bacteria ATCC 13384 and O55 and against one amebic species: .

摘要

描述了一种新型、高效、绿色、内源性水引发、无溶剂和无催化剂的超声辅助一锅法格罗布克-布莱克本-比奈梅反应/芳基亲核取代反应/环链叠氮互变异构化策略,用于合成含喹啉部分的结合型稠合双杂环咪唑或苯并[]咪唑[2,1-]噻唑以及1,5-二取代四唑(1,5-DsT),该策略能够在温和的绿色条件下一步合成两种类型的稠合杂环。对所选新合成化合物针对三种细菌物种:革兰氏阳性菌ATCC 6538和革兰氏阴性菌ATCC 13384及O55,以及针对一种阿米巴物种: 进行了抗菌和抗阿米巴活性测试。

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