Canadian Science Publishing, Canadian Journal of Chemistry, 8(73), p. 1348-1356, 1995
DOI: 10.1139/v95-166
Wiley-VCH Verlag, ChemInform, 13(27), p. no-no, 2010
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The acid-catalyzed cyclization of p-toluenesulfonamides of N-benzyl aminoacetaldehyde, or their acetalic counterparts, usually yields 1,2-dihydroisoquinolines. However, cyclization of intermediates bearing a substituent α to the carbonyl group affords 3-substituted 2-p-toluenesulfonyl tetrahydroisoquinolin-4-ol derivatives, capable of further transformation into the related 1,2,3,4-tetrahydroisoquinolines. Keywords: 3-substituted tetrahydroisoquinolines, MY336-a analog, acid-catalyzed cyclization, tetrahydroisoquinolin-4-ol derivatives.