Microwave assisted synthesis of indole-annulated dihydropyrano[3,4-c] chromene derivatives via hetero-Diels-Alder reaction

被引：30

作者：

Jha, Mukund ^{[1
]}

Guy, Stephanie ^{[1
]}

Chou, Ting-Yi ^{[1
]}

机构：

[1] Nipissing Univ, Dept Biol & Chem, N Bay, ON P1B 8L7, Canada

来源：

TETRAHEDRON LETTERS | 2011年 / 52卷 / 33期

基金：

加拿大自然科学与工程研究理事会;

关键词：

Indole; Indolin-2-one; Dihydropyran; Chromene; Benzopyran; Hetero-Diels-Alder; Knoevenagel reaction; COMBINATORIAL LIBRARIES; PRIVILEGED STRUCTURES; TERMINAL ACETYLENES; EFFICIENT SYNTHESIS; NATURAL-PRODUCTS; AQUEOUS-MEDIA;

D O I：

10.1016/j.tetlet.2011.06.052

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient two-step synthesis of indole-annulated dihydropyrano[3,4-c]chromene derivatives is achieved via Knoevenagel condensation of O-propargylated salicylaldehyde derivatives with indolin-2-ones followed by a microwave-assisted intramolecular-hetero-Diels-Alder reaction of the resulting (Z)-3-(2-(prop-2-ynyloxy)benzylidene)indolin-2-ones in the presence of 20 mol % Cul in acetonitrile. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：4337 / 4341

页数：5

共 29 条

[1] CINOGLAN.GM, 1969, J MED CHEM, V12, P531
[2] A NEW EFFICIENT AND MILD SYNTHESIS OF 2-OXINDOLES BY ONE-POT WOLFF-KISHNER LIKE REDUCTION OF ISATIN DERIVATIVES
CRESTINI, C
SALADINO, R
[J]. SYNTHETIC COMMUNICATIONS, 1994, 24 (20) : 2835 - 2841
[3] Catalysis with inorganic cations .5. Intramolecular hetero Diels-Alder versus ene reactions: Effect of magnesium perchlorate on chemoselectivity.
Desimoni, G
Faita, G
Righetti, P
Tacconi, G
[J]. TETRAHEDRON, 1996, 52 (36) : 12009 - 12018
[4] CuI/La(OTf)3 catalyzed, one-pot synthesis of isomeric ellipticine derivatives in ionic liquid
Gaddam, Vikram
Ramesh, Subburethinam
Nagarajan, Rajagopal
[J]. TETRAHEDRON, 2010, 66 (23) : 4218 - 4222
[5] Diastereoselective synthesis of cis-fused pyrano[4,5-c]pyrrole derivatives via microwave-accelerated intramolecular Knoevenagal hetero Diels-Alder reaction
Jayagobi, Mathesan
Raghunathan, Raghavachary
[J]. TETRAHEDRON-ASYMMETRY, 2010, 21 (21-22) : 2726 - 2732
[6] An efficient synthesis of pyrano [4,5-c] pyrrole derivatives through microwave-accelerated intramolecular Knoevenagal hetero Diels-Alder reaction
Jayagobi, Mathesan
Raghunathan, Raghavachary
[J]. TETRAHEDRON LETTERS, 2009, 50 (49) : 6886 - 6890
[7] Joule J.A., 2000, Science of Synthesis: Houben-Weyl Methods of Molecular Transformations, V10
[8] CATHOMYCIN .1. ISOLATION AND CHARACTERIZATION
KACZKA, EA
WOLF, FJ
RATHE, FP
FOLKERS, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (23) : 6404 - 6405
[9] Expedient Synthesis of Highly Functionalized Coumarin Derivatives through a Domino Reaction
Kathiravan, Subban
Raghunathan, Raghavachary
[J]. SYNLETT, 2010, (13) : 1927 - 1930
[10] Khoshkholgh M.J., 2008, Arkivoc, V9, P114

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