Highly stable keto-enamine salicylideneanilines

被引：291

作者：

Chong, JH ^{[1
]}

Sauer, M ^{[1
]}

Patrick, BO ^{[1
]}

MacLachlan, MJ ^{[1
]}

机构：

[1] Univ British Columbia, Dept Chem, Vancouver, BC V6T 1Z1, Canada

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 21期

关键词：

D O I：

10.1021/ol0352714

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Highly stable NH salicylideneanilines have been prepared by reaction of 1,3,5-triformylphloroglucinol with aniline derivatives. The NH form was confirmed by X-ray crystallographic data, as well as by NMR studies. A convenient one-step synthesis of triformylphloroglucinol is also reported.

引用

页码：3823 / 3826

页数：4

共 40 条

[1] Tautomerization dynamics of a model base pair in DNA [J].

Abou-Zied, OK ;

Jimenez, R ;

Romesberg, FE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (19) :4613-4614

[2] Spectroscopic and semi-empirical MO study of substituent effects on the intramolecular proton transfer in anils of 2-hydroxybenzaldehydes [J].

Alarcón, SH ;

Pagani, D ;

Bacigalupo, J ;

Olivieri, AC .

JOURNAL OF MOLECULAR STRUCTURE, 1999, 475 (2-3) :233-240

[3] C-13 NMR SPECTROSCOPIC AND AM1 STUDY OF THE INTRAMOLECULAR PROTON-TRANSFER IN ANILS OF SALICYLALDEHYDE AND 2-HYDROXYNAPHTHALENE-1-CARBALDEHYDE [J].

ALARCON, SH ;

OLIVIERI, AC ;

GONZALEZSIERRA, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1994, (05) :1067-1070

[4] Deuterium isotope effect on the solid-state thermal isomerization of photo-coloured cis-keto species of N-salicylideneaniline [J].

Amimoto, K ;

Kanatomi, H ;

Nagakari, A ;

Fukuda, H ;

Koyama, H ;

Kawato, T .

CHEMICAL COMMUNICATIONS, 2003, (07) :870-871

[5] A convenient one-step synthesis of 2-hydroxy-1,3,5-benzenetricarbaldehyde [J].

Anderson, AA ;

Goetzen, T ;

Shackelford, SA ;

Tsank, S .

SYNTHETIC COMMUNICATIONS, 2000, 30 (17) :3227-3232

[6] PHYSICOCHEMICAL PROPERTIES OF SCHIFF-BASES .4. TAUTOMERIC EQUILIBRIUM AND KINETICS OF HYDROLYSIS OF N-BENZYLIDENEANILINE DERIVATIVES [J].

CHARETTE, JJ ;

DEHOFFMANN, E .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (13) :2256-2262

[7] Excited-state amino-imino double-proton tautomerism in adenine nucleotide analogues catalyzed by carboxylic acids [J].

Chou, PT ;

Chen, YC ;

Wei, CY ;

Chen, WS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (38) :9322-9323

[8] 2,4,6-TRIS(4,5-DI-NORMAL-PROPYL-1,3-DITHIOL-2-YLIDENE)CYCLOHEXANE-1,3,5-TRIONE - SYNTHESIS, X-RAY CRYSTAL-STRUCTURE AND AMPHOTERIC REDOX PROPERTIES OF A HIGHLY DELOCALIZED HETEROCYCLIC PI-SYSTEM [J].

COFFIN, MA ;

BRYCE, MR ;

CLEGG, W .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (05) :401-402

[9] Linear and nonlinear optical properties of photochromic molecules and materials [J].

Delaire, JA ;

Nakatani, K .

CHEMICAL REVIEWS, 2000, 100 (05) :1817-1845

[10] Importance of tautomers in the chemical behavior of tetracyclines [J].

Duarte, HA ;

Carvalho, S ;

Paniago, EB ;

Simas, AM .

JOURNAL OF PHARMACEUTICAL SCIENCES, 1999, 88 (01) :111-120

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