Journal
TETRAHEDRON
Volume 70, Issue 8, Pages 1659-1690Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2014.01.008
Keywords
Furan; Cycloaddition; IMDAF; Isoindole; Wagner-Meerwein rearrangement
Categories
Funding
- Russian Foundation for Basic Research [13-03-00105a, 10-03-00177a]
- Program Molecular and cell Biology of the Presidium of the Russian Academy of Sciences
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An efficient and versatile one-pot synthesis of 3,6a-epoxyisoindoles annelated with oxazine, oxazole, thiazine, thiazole, pyrimidine fragments and with their benzoannelated analogues is presented. The method is based on tandem N-acylation/intramolecular cycloaddition (the intramolecular Diels-Alder reaction of furan, IMDAF) reaction between alpha,beta-unsaturated acid anhydrides and alpha-furyl substituted azaheterocycles. The latter can be easily prepared by condensation of diverse furfurals and 1,2- or 1,3-N,X-binucleophiles (aminoalcohols, aminothiols, diamines). The observed IMDAF reaction is stereo-selective: exo-adducts are formed exclusively with large prevalence of one of the diastereoisomers. In most cases, the condensation/N-acylation/IMDAF reaction sequence may be carried out via a one-pot domino protocol. The scope and limitations of the proposed approach are thoroughly investigated. The obtained Diels-Alder adducts are attractive and useful substrates for further transformations. Fused isoindoles can be prepared from them in one-step by aromatization of the 7-oxabicyclo[2.2.1]heptene ring. Other transformations, including halogenation, ring cleavage, and Wagner-Meerwein skeletal rearrangement, are also demonstrated. The spatial structures of the obtained compounds have been established by X-ray diffraction analyses. (C) 2014 Elsevier Ltd. All rights reserved.
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