Formamidines in synthesis. An efficient one-pot synthesis of 7-substituted indolines via intramolecular cyclization of (2-phenethyl) formamidines. An asymmetric route …

TM Sielecki, AI Meyers

Index: Sielecki, Thais M.; Meyers, A. I. Journal of Organic Chemistry, 1992 , vol. 57, # 13 p. 3673 - 3676

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Citation Number: 30

Abstract

o-Chloro-8-phenethylamines, transformed into the N-tert-butylformamidines, were found to be excellent precursors to indolines following benzyne formation. A series of methoxy- substituted o-chlorophenethylamines containing an N-alkyl or aryl substitutent were subjeded to sec-butyllithium producing the orthelithiated aromatic which subsequently lost lithium chloride at temperatures ranging from-78 to-50" C. The resulting benzyne was ...