Tetrahedron

A simplified isoquinoline synthesis

DL Boger, CE Brotherton, MD Kelley

Index: Boger, Dale L.; Brotherton, Christine E.; Kelley, Marshall D. Tetrahedron, 1981 , vol. 37, # 23 p. 3977 - 3980

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Citation Number: 33

Abstract

A simple variation of the Pomeranz-Fritsch cyclization provides a short, efficient route to isoquinolines. Treatment of benzylic halides or mesylates 1 with the sodium anion of N-tosyl aminoacetaldehyde dimethyl acetal (2) followed by acid-catalyzed cyclization provides an effective, two-step preparation of isoquinolines 4.