Investigations on synthesis of indole based constrained mimetic scaffolds through 1,3-dipolar cycloadditions of the C-(3-indolyl)-N-phenylnitrone with a variety of olefinic and allenic dipolarophiles under microwave irradiation

被引：22

作者：

Bhella, Surinderjit Singh ^{[1
]}

Pannu, Ajay Pal Singh ^{[2
]}

Elango, Munusamy ^{[3
]}

Kapoor, Ashish ^{[1
]}

Hundal, Maninder Singh ^{[2
]}

Ishar, Mohan Paul S. ^{[1
]}

机构：

[1] Guru Nanak Dev Univ, Dept Pharmaceut Sci, Bioorgan & Photochem Lab, Amritsar 143005, Punjab, India

[2] Guru Nanak Dev Univ, Dept Chem, Amritsar 143005, Punjab, India

[3] Cent Leather Res Inst, Chem Lab, Madras 600020, Tamil Nadu, India

来源：

TETRAHEDRON | 2009年 / 65卷 / 31期

关键词：

Isoxazolidines; Bis-indole; 1,3-Dipolar cycloadditions; Domino-reorganizations; Constrained mimetic scaffolds; DFT analysis; SECONDARY ORBITAL INTERACTIONS; STRUCTURE ELUCIDATION; INHIBITORS; NITRONES; ISOXAZOLIDINES; STEREOSELECTIVITIES; ROUTE; REGIOSELECTIVITIES; ESTERS; AGENTS;

D O I：

10.1016/j.tet.2009.05.093

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Monomode microwave assisted regio- and stereo-selective 1,3-dipolar cycloadditions of C-(3-indolyl)-N-phenylnitrone (19) with a number of olefinic dipolarophiles (20a-f) afford isoxazolidines (21-26) in high yields, which are conformationally constrained mimetics of indole-3-propionic acid of biological significance. Similar cycloadducts derived from addition of nitrone (19) to allenic esters (27a-c) undergo domino reorganization to afford potentially biologically active bis-indole derivatives (28, 29). The observed regio- and stereo-selectivities are analysed, inter alia, in terms of HOMO-dipole-LUMO-dipolarophile and involved secondary orbital/steric interactions in the transition states intervening these cycloadditions. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：5928 / 5935

页数：8

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