Multicomponent One-Pot Synthesis of 3-Tetrazolyl and 3-Imidazo[1,2-a]pyridin Tetrazolo[1,5-a]quinolines

被引：31
作者：
Basavanaz Unnamatla, M. V. [1 ]
Islas-Jacome, Alejandro [1 ]
Quezada-Soto, Andrea [1 ]
Ramirez-Lopez, Sandra C. [1 ]
Flores-Alamo, Marcos [2 ]
Gamez-Montano, Rocio [1 ]
机构：
[1] Univ Guanajuato, Div Ciencias Nat & Exactas, Dept Quim, Noria Alta S-N, Guanajuato 36050, Gto, Mexico
[2] Univ Nacl Autonoma Mexico, Inst Quim, Circuito Exterior S-N,Ciudad Univ, Coyoacan 04510, Cdmx, Mexico
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 21期
关键词：
BIS-HETEROCYCLIC COMPOUNDS; RADICAL CYCLIZATION; UGI-AZIDE; DERIVATIVES; TETRAZOLES; DIVERSITY; CHEMISTRY;
D O I：
10.1021/acs.joc.6b01576
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of 18 3-tetrazolyl-tetrazolo[1,5-a]-quinolines were synthesized in 21-90% yields via a novel one-pot Ugi-azide/SNAr/ring-chain azido-tautomerization process. We report also the synthesis of 10 3-imidazo[1,2-a]pyridin-tetrazolo[1,5-a]quinolines in 28-94% yields via a novel one-pot Groebke-Blackburn-Bienayme/SNAr/ring-chain azido-tautomerization process. Both synthetic strategies involve the use of microwaves or ultrasound, and catalyst-free conditions. Finally, we show the synthesis of the tetrazolo[1,5-a]quinoline-3-carbaldehyde and tetrazolo [1,5-a]quinoline-3-dimethyl acetal at room temperature in methanol as solvent.
引用
收藏
页码：10576 / 10583
页数：8
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