One-pot synthesis of photochromic naphthopyrans in the solid state

Koichi Tanaka; Hiroko Aoki; Hiroyuki Hosomi; Shigeru Ohba

doi:10.1021/ol006038y

One-pot synthesis of photochromic naphthopyrans in the solid state

Koichi Tanaka, Hiroko Aoki, Hiroyuki Hosomi, Shigeru Ohba

Research output: Contribution to journal › Article › peer-review

64 Citations (Scopus)

Abstract

matrix presented 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.

Original language	English
Pages (from-to)	2133-2134
Number of pages	2
Journal	Organic Letters
Volume	2
Issue number	14
DOIs	https://doi.org/10.1021/ol006038y
Publication status	Published - 2000 Jul 13
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "One-pot synthesis of photochromic naphthopyrans in the solid state",

abstract = "matrix presented 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.",

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doi = "10.1021/ol006038y",

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journal = "Organic Letters",

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T1 - One-pot synthesis of photochromic naphthopyrans in the solid state

AU - Tanaka, Koichi

AU - Aoki, Hiroko

AU - Hosomi, Hiroyuki

AU - Ohba, Shigeru

PY - 2000/7/13

Y1 - 2000/7/13

N2 - matrix presented 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.

AB - matrix presented 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.

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One-pot synthesis of photochromic naphthopyrans in the solid state

Abstract

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