Facile access to novel chromeno-2,6,9-trioxabicyclo[3.3.1] nonadienes via tandem nucleophilic substitution and [4+2] hetero Diels-Alder reaction: experimental and theoretical study

被引：14

作者：

Jaggavarapu, Satyanarayana Reddy ^{[1
]}

Kamalakaran, Anand Solomon ^{[1
]}

Gayatri, Gaddamanugu ^{[2
]}

Shukla, Matsyendranath ^{[3
]}

Dorai, Kavita ^{[3
]}

Gaddamanugu, Gopikrishna ^{[1
]}

机构：

[1] Sankar Fdn Res Inst, Dept Chem, Naiduthota 530047, Vishakapatnam, India

[2] Indian Inst Chem Technol, Mol Modelling Div, Hyderabad 500607, Andhra Pradesh, India

[3] Indian Inst Sci Educ & Res, Chandigarh, India

来源：

TETRAHEDRON | 2013年 / 69卷 / 09期

关键词：

Chromeno-2,6,9-trioxabicyclo[3.3.1]nonadienes; 4-Chloro-3-formylcoumarin; o-Hydroxyacetophenones; DFT; Tandem; CYCLOADDITION REACTIONS; ABSOLUTE-CONFIGURATION; ANTIFUNGAL METABOLITES; CRYSTAL-STRUCTURE; PREUSSOMERINS; FUNGUS; DERIVATIVES; (+/-)-PREUSSOMERIN-K; ANTIBACTERIAL; COMPLEX;

D O I：

10.1016/j.tet.2013.01.002

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient synthesis of novel chromeno-2,6,9-trioxabicyclo-[3.3.1]nonadienes (CTOBN) scaffolds was achieved by mild base mediated reaction of 4-chloro-3-formylcoumarin and o-hydroxyacetophenones. The structure of the product was confirmed by X-ray analysis and the proposed mechanism was validated computationally at B3LYP/6-31G(d) level. (c) 2013 Elsevier Ltd. All rights reserved.

引用

页码：2142 / 2149

页数：8

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