One-Pot Synthesis of Photochromic Naphthopyrans in the Solid State

16 June 2000

journal article
research article
Published by American Chemical Society (ACS) in Organic Letters

Vol. 2 (14) , 2133-2134
https://doi.org/10.1021/ol006038y

Abstract

P-TsOH-catalyzed condensation reactions of 1,1-diaryl-2-propyn-1-ol (1) and 2-naphthol (2) in the solid state gave 3,3-diaryl-3H-naphtho[2,1-b]pyran (6) via Claisen rearrangement. Similar reactions of 1 with 2,6- (7) and 2,7-dihydroxynaphthalenes (8) afforded naphthodipyrane derivatives 9 and 10, respectively. Bis-naphthopyran derivatives 12 were also obtained by the reaction of 1,1,6,6-tetraaryl-2,5-hexadiyn-1,6-diol (11) and 2-naphthol (2) in the solid state.

Keywords

NAPHTHOPYRANS
PHOTOCHROMIC
POT
BIS
DIOL
HEXADIYN
DIHYDROXYNAPHTHALENES
PROPYN

This publication has 2 references indexed in Scilit:

Solvent-Free Organic Synthesis
Chemical Reviews, 2000
Photochromism of Diarylnaphthopyrans
Molecular Crystals and Liquid Crystals, 1994