Syntheses of 3-Substituted 2, 3-Dihydrobenzofuranes, 1, 2-Dihydronaphtho (2, 1-b) furanes, and 2, 3-Dihydro-1 H-indoles by Tandem Ring Closure-SRN1 Reactions

SE Vaillard, A Postigo, RA Rossi

Index: Vaillard, Santiago E.; Postigo, Al; Rossi, Roberto A. Journal of Organic Chemistry, 2002 , vol. 67, # 24 p. 8500 - 8506

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Citation Number: 26

Abstract

3-Substituted 2, 3-dihydrobenzofuranes (7a-c), 1, 2-dihydronaphtho (2, 1-b) furanes (10a-c), and N-substituted 2, 3-dihydro-1 H-indoles (8a-c, 9a, b) are obtained in very good yields by SRN1 photostimulated reactions in liquid ammonia from adequate haloaromatic compounds ortho-substituted with a suitable double bond (3a, b; 4a, b; 5a; 6a, b) and Me3Sn-, Ph2P-, and-CH2NO2 anions. The novelty of the work involves the versatile application of a 5-exo ...