A versatile synthesis of fused triazolo derivatives by sequential Ugi/alkyne-azide cycloaddition reactions

被引：118

作者：

Akritopoulou-Zanze, I ^{[1
]}

Gracias, V ^{[1
]}

Djuric, SW ^{[1
]}

机构：

[1] Abbott Labs, Abbott Pk, IL 60064 USA

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 46期

关键词：

multi-component reactions; Ugi; intramolecular azide-alkyne cycloaddition; fused triazolo derivatives; dihydrotriazolo [1,5-a]pyrazinones; triazolobenzodiazepines; sequential Ugi/IAAC; fused heterocycles;

D O I：

10.1016/j.tetlet.2004.09.117

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report a facile synthesis of fused dihydrotriazolo[1,5-alpha]pyrazinones and triazolobenzodiazepines by an Ugi/alkyne-azide cycloaddition synthetic sequence. The coupling of the Ugi multi-component reaction with the intramolecular alkyne-azide cycloaddition provides access to highly functionalized heterocyclic ring systems in two steps from easily available starting materials in excellent overall yields. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：8439 / 8441

页数：3

共 33 条

[1] Synthesis of novel fused isoxazoles and isoxazolines by sequential Ugi/INOC reactions
Akritopoulou-Zanze, I
Gracias, V
Moore, JD
Djuric, SW
[J]. TETRAHEDRON LETTERS, 2004, 45 (17) : 3421 - 3423
[2] Alvarez SG, 1997, SYNTHESIS-STUTTGART, P413
[3] Application of tandem Ugi reaction/ring-closing metathesis in multicomponent synthesis of unsaturated nine-membered lactams
Banfi, L
Basso, A
Guanti, G
Riva, R
[J]. TETRAHEDRON LETTERS, 2003, 44 (41) : 7655 - 7658
[4] Short and diverse route toward complex natural product-like macrocycles
Beck, B
Larbig, G
Mejat, B
Magnin-Lachaux, M
Picard, A
Herdtweck, E
Dömling, A
[J]. ORGANIC LETTERS, 2003, 5 (07) : 1047 - 1050
[5] Highly substituted pyrrolidinones and pyridones by 4-CR/2-CR sequence
Beck, B
Picard, A
Herdtweck, E
Dömling, A
[J]. ORGANIC LETTERS, 2004, 6 (01) : 39 - 42
[6] BERTRLLI L, 1988, FARMACO, V53, P305
[7] BROGGINI G, 1995, SYNTHESIS-STUTTGART, P647
[8] BROGGINI G, 1997, J CHEM RES, V10, P380
[9] QUINAZOLINES AND 1,4-BENZODIAZEPINES .70. UPSILON-TRIAZOLO[1,5-ALPHA] [1,4]BENZODIAZEPINES
COFFEN, DL
FRYER, RI
KATONAK, DA
WONG, F
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (07) : 894 - 897
[10] Solid-phase synthesis of natural product-like macrocycles by a sequence of Ugi-4CR and SNAr-based cycloetherification
Cristau, P
Vors, JP
Zhu, JP
[J]. TETRAHEDRON LETTERS, 2003, 44 (30) : 5575 - 5578

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