A detailed investigation of the multicomponent reaction of salicylaldehyde, ethyl acetoacetate and isocyanides under microwave heating

被引：16

作者：

Amanpour, Tayebeh ^{[1
,2
]}

Zangger, Klaus ^{[1
]}

Belaj, Ferdinand ^{[1
]}

Bazgir, Ayoob ^{[2
]}

Dallinger, Doris ^{[1
]}

Kappe, C. Oliver ^{[1
]}

机构：

[1] Graz Univ, Inst Chem, NAWI Graz, A-8010 Graz, Austria

[2] Shahid Beheshti Univ, Dept Chem, Tehran 1983963113, Iran

来源：

TETRAHEDRON | 2015年 / 71卷 / 39期

关键词：

Autoxidation; Coumarins; Isocyanides; Microwave heating; Multicomponent reactions; ONE-POT; RING TRANSFORMATION; DRUG DISCOVERY; CHEMISTRY; COUMARINS; LIBRARIES; CONSTRUCTION; AUTOXIDATION; PRODUCTS; DESIGN;

D O I：

10.1016/j.tet.2014.12.002

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New insights into the cyclocondensation reaction of salicylaldehyde, ethyl acetoacetate and isocyanides are reported. Depending on the reaction conditions either the previously reported 5-hydroxy-Nsubstituted-2H-dihydrochromeno[3,4-c]pyrrol-2-ones or the novel 2-imino-5-hydroperoxy-5-methyl-2H-dihydrochromeno[3,4-c]furans were obtained. Although suggested as intermediates in previously proposed reaction mechanisms, these hydroperoxides are not obtained when the reaction is performed under open vessel reflux conditions, but are the main product when conducted in a closed vessel using either microwave or conventional heating. Thorough NMR studies and X-ray crystallography confirm the structure of the generated hydroperoxy products. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：7159 / 7169

页数：11

共 71 条

[11] Recent developments in isocyanide based multicomponent reactions in applied chemistry
Dömling, A
[J]. CHEMICAL REVIEWS, 2006, 106 (01) : 17 - 89
[12] Recent advances in isocyanide-based multicomponent chemistry
Dömling, A
[J]. CURRENT OPINION IN CHEMICAL BIOLOGY, 2002, 6 (03) : 306 - 313
[13] Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO
[14] 2-U
[15] Chemistry and Biology Of Multicomponent Reactions
Domling, Alexander
Wang, Wei
Wang, Kan
[J]. CHEMICAL REVIEWS, 2012, 112 (06) : 3083 - 3135
[16] Beyond the Ugi reaction: less conventional interactions between isocyanides and iminium species
El Kaim, Laurent
Grimaud, Laurence
[J]. TETRAHEDRON, 2009, 65 (11) : 2153 - 2171
[17] STEROIDAL ANALOGUES OF UNNATURAL CONFIGURATION .2. AUTOXIDATION OF NEUTRAL DELTA17[20]-ENOLS - METHOD OF 17-HYDROXYLATION
ENSLIN, PR
[J]. TETRAHEDRON, 1971, 27 (10) : 1909 - &
[18] A facile reaction involving zwitterionic intermediates for the synthesis of 5-hydroxy-2H-pyrrol-2-one derivatives
Fan, Ming-Jin
Qian, Bo
Zhao, Lian-Biao
Liang, Yong-Min
[J]. TETRAHEDRON, 2007, 63 (36) : 8987 - 8992
[19] PHOTOCHEMICAL-REACTION OF PHTHALIMIDES AND DICYANOPHTHALIMIDES WITH BENZYLIC DONORS
FRECCERO, M
FASANI, E
ALBINI, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (07) : 1740 - 1745
[20] Strategies for Innovation in Multicomponent Reaction Design
Ganem, Bruce
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (03) : 463 - 472

← 1 2 3 4 5 6 7 8 →