Tetrahedron letters

Synthesis of 1, 2, 3, 4-tetrahydroquinolines and 1, 2, 3, 4-tetrahydro-1, 6-naphthyridines by a directed lithiation reaction

JN Reed, J Rotchford, D Strickland

Index: Reed, J. Norman; Rotchford, Judy; Strickland, Dean Tetrahedron Letters, 1988 , vol. 29, # 45 p. 5725 - 5728

Full Text: HTML

Citation Number: 45

Abstract

Abstract N-(tert-butoxycarbonyl) anilines (7), are easily converted in a one pot reaction sequence into the N-(tert-butoxycarbonyl)-1, 2, 3, 4-tetrahydroquinolines (8), by directed ortho lithiation followed by reaction with 1-chloro-3-iodopropane, hence providing a new versatile quinoline ring nucleus synthesis. In an analogous reaction 2-N-(tert- butoxycarbonyl)-and an 2-N-(pivaloylamino) pyridine are converted to 1, 2, 3, 4-tetrahydro ...