Synthesis and Diels-Alder reactions of the benzo[4,5]thieno[2,3-c]pyrrole ring system

被引：7

作者：

Sha, CK ^{[1
]}

Hsu, HY ^{[1
]}

Cheng, SY ^{[1
]}

Kuo, YL ^{[1
]}

机构：

[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu 300, Taiwan

来源：

TETRAHEDRON | 2003年 / 59卷 / 09期

关键词：

benzo[4,5]thieno[2,3-d]pyridazine; retro-malonate addition; 1,3-dipolar cycloaddition-cycloreversion; Knoevenagel condensation; dibenzothiophene;

D O I：

10.1016/S0040-4020(03)00074-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first synthesis of the parent compound of the benzo[4,5]thieno[2,3-c]pyrrole ring system and its derivatives, as well as their Diels-Alder reactions with DMAD and N-phenylmaleimide are reported. A new synthesis of the benzo[4,5]thieno[2,3-d]pyridazine ring system is also described. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：1477 / 1481

页数：5

相关论文

共 12 条

[1] ELECTROCHEMICAL POLYMERIZATION OF N-SUBSTITUTED THIENO[2,3-C]PYRROLE [J].

CHIOU, YC ;

SHA, CK ;

CHEN, HF .

SYNTHETIC METALS, 1992, 48 (01) :33-38

[2] CONDENSED THIOPHEN RING SYSTEMS .5. SYNTHESIS, REACTIONS, AND STABILITY OF 2-METHYL-3-BENZO[B]THIENYL-LTHIUM AND 2-METHYLTHIO-3-BENZO[B]THIENYL-LITHIUM AND RELATED COMPOUNDS [J].

DICKINSON, RP ;

IDDON, B .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (01) :182-+

[3] BENZO[1]THIENO(2,3-D)PYRIDAZINES .1. STUDY ON CONDITIONS FOR SYNTHESIS OF BENZOTHIENOPYRIDAZINES [J].

DORE, G ;

ROBBA, M ;

BONHOMME, M .

TETRAHEDRON, 1972, 28 (09) :2553-&

[4]

Fringuelli F., 1990, DIENES DIELS ALDER R, P125

[5] PREPARATION AND DIELS-ALDER REACTIVITY OF BENZOTHIENO[2,3-C]-PYRAN-3-ONES, AND BENZOTHIENO[3,2-C]-PYRAN-3-ONES, BENZOTHIOPHENE-2,3-QUINODIMETHANE ANALOGS - SYNTHESIS OF DIBENZOTHIOPHENES [J].

JACKSON, PM ;

MOODY, CJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (03) :681-687

[6] ELECTROCHEMICAL SYNTHESIS AND PRELIMINARY CHARACTERIZATION OF POLY(THIENO[3,2-B]PYRROLE) [J].

LAZZARONI, R ;

RIGA, J ;

VERBIST, JJ ;

CHRISTIAENS, L ;

RENSON, M .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (14) :999-1000

[7]

Ono N, 1994, J CHEM SOC CHEM COMM, P1019

[8]

ROBBA M, 1969, CR ACAD SCI C CHIM, V268, P256

[9]

Sha C.-K., 1996, ADV NITROG HETERCYC, V2, P147

[10] SYNTHESIS AND TRAPPING OF 4H-THIENO[3,4-C]PYRROLE AND 5H-THIENO[3,4-C]PYRROLE [J].

SHA, CK ;

TSOU, CP .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (21) :3065-3070