Synthesis and functionalization of thiophene congeners of Troger's base

被引：12

作者：

Kobayashi, T ^{[1
]}

Moriwaki, T ^{[1
]}

Tsubakiyama, M ^{[1
]}

Yoshida, S ^{[1
]}

机构：

[1] Shinshu Univ, Fac Sci, Dept Chem, Matsumoto, Nagano 3908621, Japan

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2002年 / 17期

关键词：

D O I：

10.1039/b205227j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Thiophene congeners of Troger's base were prepared by the reactions of 3-aminothiophenes and formaldehyde. Treatment of the thiophene congeners with BuLi or LDA resulted in the regioselective formation of the dianion at the 2- and 7-positions, which reacted with a variety of electrophiles such as trimethylsilyl chloride, iodine, NBS, DMF, benzophenone, and benzaldehyde. This reaction opens up a facile and versatile entry for a Troger's base skeleton with a variety of functional groups.

引用

页码：1963 / 1967

页数：5

共 45 条

[1] CHEMISTRY OF SYNTHETIC RECEPTORS AND FUNCTIONAL-GROUP ARRAYS .10. ORDERLY FUNCTIONAL-GROUP DYADS - RECOGNITION OF BIOTIN AND ADENINE-DERIVATIVES BY A NEW SYNTHETIC HOST [J].

ADRIAN, JC ;

WILCOX, CS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (20) :8055-8057

[2] CHEMISTRY OF SYNTHETIC RECEPTORS AND FUNCTIONAL-GROUP ARRAYS .15. EFFECTS OF ADDED WATER ON THERMODYNAMIC ASPECTS OF HYDROGEN-BOND-BASED MOLECULAR RECOGNITION IN CHLOROFORM [J].

ADRIAN, JC ;

WILCOX, CS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) :678-680

[3] THE CHEMISTRY OF SYNTHETIC RECEPTORS AND FUNCTIONAL GROUP ARRAYS .19. GENERAL EFFECTS OF BINDING-SITE WATER EXCLUSION ON HYDROGEN-BOND BASED MOLECULAR RECOGNITION SYSTEMS - A CLOSED BINDING-SITE IS LESS AFFECTED BY ENVIRONMENTAL-CHANGES THAN AN OPEN SITE [J].

ADRIAN, JC ;

WILCOX, CS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (04) :1398-1403

[4]

BAG BG, 1995, CURR SCI INDIA, V68, P279

[5] A CONVENIENT METHOD FOR THE SYNTHESIS OF TROGER BASE ANALOGS [J].

BAG, BG ;

MAITRA, U .

SYNTHETIC COMMUNICATIONS, 1995, 25 (12) :1849-1856

[6]

Bag BG, 1999, ANGEW CHEM INT EDIT, V38, P3713, DOI 10.1002/(SICI)1521-3773(19991216)38:24<3713::AID-ANIE3713>3.0.CO

[7]

2-#

[8] AN EASY SYNTHESIS OF 3-AMINOTHIOPHENE AND 3-NITROTHIOPHENE [J].

BARKER, JM ;

HUDDLESTON, PR ;

WOOD, ML .

SYNTHETIC COMMUNICATIONS, 1995, 25 (23) :3729-3734

[9] ISOLATION OF A HIGHLY FUNCTIONALIZED TROGER BASE DERIVATIVE VIA A NOVEL REACTION [J].

BECKER, DP ;

FINNEGAN, PM ;

COLLINS, PW .

TETRAHEDRON LETTERS, 1993, 34 (12) :1889-1892

[10] Unusual cyclization of 1-thianaphthenone-3-dioxide-1,1 to a 1,5-diazabicyclo[3.3.1]nonane - a heterocyclic analogue of a Troger's base [J].

Cekavicus, B ;

Liepinsh, E ;

Vigante, B ;

Sobolevs, A ;

Ozols, J ;

Duburs, G .

TETRAHEDRON LETTERS, 2001, 42 (25) :4239-4241

← 1 2 3 4 5 →