INVERSE-ELECTRON-DEMAND DIELS-ALDER REACTIONS OF CONDENSED PYRIDAZINES .2. SYNTHESIS OF ISOQUINOLINE DERIVATIVES FROM PYRIDO[3,4-D]PYRIDAZINES

被引：9

作者：

HAIDER, N

机构：

[1] Institute of Pharmaceutical Chemistry, A-1090 Vienna

来源：

TETRAHEDRON | 1992年 / 48卷 / 35期

关键词：

D O I：

10.1016/S0040-4020(01)88258-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Employment of pyrido[3,4-d]pyridazine derivatives 1, 2, 3 as aza-dienes in inverse-electron-demand Diels-Alder reactions with 1-pyrrolidino-1-cyclopentene or its six-membered homologue, respectively, was found to provide an easy access to the isoquinolines 5, 7, 9, 11, 13, 15 after aromatisation of intermediate mixtures of regioisomeric dihydroisoquinoline derivatives.

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页码：7173 / 7184

页数：12

相关论文

共 20 条

[1] THE DIELS-ALDER REACTION OF 1-VINYLNAPHTHALENE WITH ALPHA,BETA-UNSATURATED AND ALPHA,BETA,GAMMA,DELTA-UNSATURATED ACIDS AND DERIVATIVES [J].

BACHMANN, WE ;

DENO, NC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (09) :3062-3072

[2] PYRIDAZINES .41. SYNTHESIS OF NOVEL PYRIDO[3,4-D]PYRIDAZINE DERIVATIVES FROM 4,5-DISUBSTITUTED PYRIDAZINES [J].

BOAMAH, PY ;

HAIDER, N ;

HEINISCH, G .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1989, 26 (04) :933-939

[3]

Boger D. L., 1987, HETERO DIELS ALDER M

[4] DIELS-ALDER REACTIONS OF HETEROCYCLIC AZADIENES - SCOPE AND APPLICATIONS [J].

BOGER, DL .

CHEMICAL REVIEWS, 1986, 86 (05) :781-793

[5] DIELS-ALDER REACTIONS OF AZADIENES [J].

BOGER, DL .

TETRAHEDRON, 1983, 39 (18) :2869-2939

[6] PYRIDAZINES .8. 4,5-DIACYLPYRIDAZINES - SYNTHESIS AND CONVERSION TO 1,4-DIARYL OR 1,4-DIALKYL-PYRIDAZINO[4,5-D]PYRIDAZINES [J].

BRAUN, M ;

HANEL, G ;

HEINISCH, G .

MONATSHEFTE FUR CHEMIE, 1978, 109 (01) :63-71

[7] REACTIONS OF TETRAZINES WITH UNSATURATED COMPOUNDS - A NEW SYNTHESIS OF PYRIDAZINES [J].

CARBONI, RA ;

LINDSEY, RV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (16) :4342-4346

[8] THE INVERSE ELECTRON DEMAND DIELS-ALDER REACTION OF 3-(METHYLSULFONYL)-1,2,4-TRIAZINE AND ENAMINES - ISOLATION OF CRYSTALLINE INTERMEDIATES AND AN IMPROVED SYNTHESIS OF 1-(METHYLSULFONYL)TETRAHYDROISOQUINOLINES [J].

CHENARD, BL ;

RONAU, RT ;

SCHULTE, GK .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (21) :5175-5177

[9] THE DEVELOPMENT AND USE OF QUANTUM-MECHANICAL MOLECULAR-MODELS .76. AM1 - A NEW GENERAL-PURPOSE QUANTUM-MECHANICAL MOLECULAR-MODEL [J].

DEWAR, MJS ;

ZOEBISCH, EG ;

HEALY, EF ;

STEWART, JJP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (13) :3902-3909

[10] RECOGNITION OF STEREOCHEMICAL PATHS BY ORBITAL INTERACTION [J].

FUKUI, K .

ACCOUNTS OF CHEMICAL RESEARCH, 1971, 4 (02) :57-&