Synthesis of 1-(1H-Tetrazol-5-yl)-2H-isoindole Derivatives through Ugi Four-Component and Silver-Catalyzed Reactions

被引：12

作者：

Wu, Ran ^{[1
]}

Gao, Shang ^{[1
]}

Chen, Xu ^{[1
]}

Yang, Guanghui ^{[1
]}

Pan, Lingling ^{[1
]}

Hu, Gaobo ^{[1
]}

Jia, Ping ^{[1
]}

Zhong, Weihui ^{[1
]}

Yu, Chuanming ^{[1
]}

机构：

[1] Zhejiang Univ Technol, Minist Educ,Coll Pharmaceut Sci, Synerget Innovat Ctr Yangtze River Delta Reg Gree, Key Lab Green Pharmaceut Technol & Related Equipm, Hangzhou 310014, Zhejiang, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 16期

基金：

中国国家自然科学基金;

关键词：

Multicomponent reactions; Cyclization; Nitrogen heterocycles; Alkynes; Silver; MULTICOMPONENT REACTIONS; 3-COMPONENT REACTION; ORGANIC-SYNTHESIS; N'-(2-ALKYNYLBENZYLIDENE)HYDRAZIDE; CYCLIZATION; TRIFLATE; 2-ALKYNYLBENZALDEHYDE; GENERATION; CHEMISTRY; CASCADE;

D O I：

10.1002/ejoc.201402098

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile and efficient one-pot, two-step synthesis of 1,2-disubstituted 3-(1H-tetrazol-5-yl)-2H-isoindoles through Ugi four-component reaction/AgNO3-catalyzed reaction of 2-alkynylbenzaldehydes, amines, isonitriles, and Me3SiN3 is described. This transformation proceeds through 5-exo-dig cyclization, [1,3]-H shift, and [1,5]-H shift to generate the products in moderate to excellent yields.

引用

页码：3379 / 3386

页数：8

共 65 条

[1] Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes
Alonso, F
Beletskaya, IP
Yus, M
[J]. CHEMICAL REVIEWS, 2004, 104 (06) : 3079 - 3159
[2] [Anonymous], 2001, ANGEW CHEM
[3] Arya P, 2001, ANGEW CHEM INT EDIT, V40, P339, DOI 10.1002/1521-3773(20010119)40:2<339::AID-ANIE339>3.0.CO
[4] 2-J
[5] Direct Mannich and nitro-Mannich reactions with non-activated imines:: AgOTf-catalyzed addition of pronucleophiles to ortho-alkynylaryl aldimines leading to 1,2-dihydroisoquinolines
Asao, N
Yudha, S
Nogami, T
Yamamoto, Y
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (34) : 5526 - 5528
[6] Asao N., 2005, ANGEW CHEM, V117, P5662
[7] Coupling Isocyanide-Based Multicomponent Reactions with Aliphatic or Acyl Nucleophilic Substitution Processes
Banfi, Luca
Riva, Renata
Basso, Andrea
[J]. SYNLETT, 2010, (01) : 23 - 41
[8] A Marriage of Convenience: Combining the Power of Isocyanide-Based Multicomponent Reactions with the Versatility of (Hetero)norbornene Chemistry
Basso, Andrea
Banfi, Luca
Riva, Renata
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (10) : 1831 - 1841
[9] Beck A., Patent US, Patent No. [4808604A28, 4808604]
[10] Silver and Gold Catalysis for Cycloisomerization Reactions
Belmont, Philippe
Parker, Evelyne
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (35) : 6075 - 6089

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