Tetrahedron Letters

Novel synthesis of 2, 2-dialkyl-3-dialkylamino-2, 3-dihydro-1H-naphtho [2, 1-b] pyrans

PJJ Huang, TS Cameron, A Jha

Index: Huang, Po-Jung Jimmy; Stanley Cameron; Jha, Amitabh Tetrahedron Letters, 2009 , vol. 50, # 1 p. 51 - 54

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Citation Number: 26

Abstract

2, 2-Dialkyl-3-dialkylamino-2, 3-dihydro-1H-naphtho [2, 1-b] pyrans were prepared from 2- naphthol, a secondary amine, and 3-hydroxy-2, 2-dialkylpropanal in the presence of a catalytic amount of p-toluenesulfonic acid. This one-pot reaction involves retro-aldol disintegration of 3-hydroxy-2, 2-dialkylpropanal followed by formation of a Mannich base intermediate from 2-naphthol, a secondary amine, and formaldehyde (retro-aldol product). ...