Synthesis and reactivity of formyl-substituted photochromic 3,3-diphenyl-[3H]-naphtho[2,1-b]pyrans

被引：31

作者：

Chamontin, K ^{[1
]}

Lokshin, V ^{[1
]}

Rossollin, V ^{[1
]}

Samat, A ^{[1
]}

Guglielmetti, R ^{[1
]}

机构：

[1] Univ Mediterranee, Fac Sci Luminy, CNRS, F-13288 Marseille 9, France

来源：

TETRAHEDRON | 1999年 / 55卷 / 18期

关键词：

D O I：

10.1016/S0040-4020(99)00245-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthetic accesses to formylated photochromic 3,3-diphenyl-[3H]-naphthopyrans (or 2H-benzochromenes) are developed through classical cyclization between appropriate hydroxynaphthaldehydes and 1,1-diphenylpropyne-1-ol and also via substituent transformations on the naphthopyran skeleton including bromine/lithium exchange and the oxidation of an hydroxymethyl group. Examples of formyl group reactivity (Wittig and Knoevenagel reactions, imine formation) from these compounds are given, showing their interest in the subsequent preparation of supramolecular systems involving a photoreactive entity. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：5821 / 5830

页数：10

共 26 条

[1] ALBEROLA A, 1994, HETEROCYCLES, V38, P819
[2] DISSYMMETRIC CALIX[4]ARENES WITH C4-SYMMETRY AND C2-SYMMETRY - SYNTHESIS, X-RAY STRUCTURES, CONFORMATIONAL FIXATION, AND H-1-NMR SPECTROSCOPIC STUDIES
ANDREETTI, GD
BOHMER, V
JORDON, JG
TABATABAI, M
UGOZZOLI, F
VOGT, W
WOLFF, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15) : 4023 - 4032
[3] PHOTOCHROMISM OF SYNTHETIC AND NATURALLY OCCURRING 2H-CHROMENES AND 2H-PYRANS
BECKER, RS
MICHL, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (24) : 5931 - &
[4] A convenient synthesis of 6-substituted-2,2-dimethyl-2H-1-benzopyrans
Ding, CZ
[J]. SYNTHETIC COMMUNICATIONS, 1996, 26 (22) : 4267 - 4273
[5] SYNTHESIS AND REACTIVITY OF SOME 4-BROMO- 2H-CHROMENES AND 2H-THIOCHROMENES
GABBUTT, CD
HARTLEY, DJ
HEPWORTH, JD
HERON, BM
KANJIA, M
RAHMAN, MM
[J]. TETRAHEDRON, 1994, 50 (08) : 2507 - 2522
[6] GUGLIELMETTI R, 1990, STUD ORG CHEM, V40, P314
[7] Photochromic behaviour of bis[4-(N,N-dimethylamino)phenyl]-substituted 3H-naphtho[2,1-b]pyran and 2H-1-benzopyran
Harie, G
Samat, A
Guglielmetti, R
DeKeukeleire, D
Saeyens, W
VanParys, I
[J]. TETRAHEDRON LETTERS, 1997, 38 (17) : 3075 - 3078
[8] Fluorine-substituted derivatives of the carcinogenic dihydrodiol and diol epoxide metabolites of 7-methyl-, 12-methyl- and 7,12-dimethylbenz[a]anthracene
Harvey, RG
Cortez, C
[J]. TETRAHEDRON, 1997, 53 (21) : 7101 - 7118
[9] Hepworth J.D., 1984, COMPREHENSIVE HETERO, V3, P737, DOI DOI 10.1016/B978-008096519-2.00046-1
[10] The diazotisation of 1-amino-2-hydroxy-4-cyanonaphthalene and the preaparation of 4-cyano-2-naphthol.
Hodgson, HH
Birtwell, S
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1944, : 539 - 540

← 1 2 3 →