PREPARATION OF 1-SUBSTITUTED-3,4-DIHYDRONAPHTHALENE-2-CARBOXALDEHYDE N,N-DIMETHYLHYDRAZONES BY PALLADIUM(0) COUPLING, AND THEIR ELECTROCYCLIC RING-CLOSURE

被引：22

作者：

GILCHRIST, TL

HEALY, MAM

机构：

[1] Chemistry Department, University of Liverpool, Liverpool, L69 3BX

来源：

TETRAHEDRON | 1993年 / 49卷 / 12期

关键词：

D O I：

10.1016/S0040-4020(01)86333-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

I-Bromo-3,4-dihydronaphthalene-2-carboxaldehyde 2 has been converted by three methods, each involving halogen-metal exchange and palladium(0) catalysed cross coupling, into N,N-dimethylhydrazones of 1-aryl- and 1-vinyl-3,4-dihydronaphthalene-2-carboxaldehydes. The NN-dimethylhydrazone 10 of the aldehyde 2 undergoes efficient bromine-lithium exchange with butyllithium, as does 2-bromobenzaldehyde N,N-dimethylhydrazone 17. The dimethylhydrazones of 1-vinyl-3,4-dihydronaphthalene-2-carboxaldehydes were not isolated but underwent electrocyclic ring closure followed by loss of dimethylamine in solution to give 5,6-dihydrobenz[f]isoquinolines. 1-Aryl-3,4-dihydronaphthalene-2-carboxaldehyde NN-dimethylhydrazones also cyclised in the same way when subjected to vapour phase pyrolysis.

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页码：2543 / 2556

页数：14

相关论文

共 34 条

[1] SYNTHESIS OF 4,5,6,7-TETRAHYDRO-1(3H)-ISOBENZOFURANONES BY REACTION OF N,N-DIMETHYL-2-LITHIO-1-CYCLOHEXENECARBOXAMIDE WITH ALDEHYDES AND KETONES [J].

BAKER, WR ;

COATES, RM .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (06) :1022-1024

[2] ON ATTEMPTED DIELS-ALDER REACTION OF 1-ETHOXYCARBONYLINDOLE-3-CARBOXALDEHYDE N,N-DIMETHYLHYDRAZONE [J].

BISWAS, GK ;

NATH, AC ;

MUKHERJEE, B ;

PATRA, A ;

CHAKRABARTY, M .

TETRAHEDRON LETTERS, 1992, 33 (01) :117-118

[3]

BUCHI G, 1991, J ORG CHEM, V56, P2605

[4] ON THE THERMAL-BEHAVIOR OF SCHIFF-BASES OF RETINAL AND ITS ANALOGS - 1,2-DIHYDROPYRIDINE FORMATION VIA 6-PI-ELECTRON ELECTROCYCLIZATION OF 13-CIS ISOMERS [J].

DELERA, AR ;

REISCHL, W ;

OKAMURA, WH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (11) :4051-4063

[5] SYNTHESIS OF 3-SUBSTITUTED FURANS BY DIRECTED LITHIATION AND PALLADIUM CATALYZED COUPLING [J].

ENNIS, DS ;

GILCHRIST, TL .

TETRAHEDRON, 1990, 46 (07) :2623-2632

[6] [3,2] SIGMATROPIC REARRANGEMENTS OF SOME ALLYLIC OXOSULFONIUM YLIDES - A ROUTE TO TRIENES AND AZATRIENES, AND THEIR CYCLIC ISOMERS [J].

FARAGHER, R ;

GILCHRIST, TL ;

SOUTHON, IW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (08) :2352-2356

[7] SYNTHESIS OF FUSED PYRIDINES BY ELECTROCYCLIC RING-CLOSURE OF ALDEHYDE N,N-DIMETHYLHYDRAZONES [J].

GILCHRIST, TL ;

HEALY, MAM .

TETRAHEDRON LETTERS, 1990, 31 (40) :5807-5810

[8] SYNTHESIS OF AROMATIC STEROIDS BY PALLADIUM(O) COUPLING AND ELECTROCYCLIC RING-CLOSURE [J].

GILCHRIST, TL ;

SUMMERSELL, RJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (09) :2603-2606

[9] FORMATION OF A 12-AZASTEROID BY 1-AZATRIENE CYCLIZATION [J].

GILCHRIST, TL ;

HEALY, MAM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (07) :749-750

[10] SYNTHESIS OF CHRYSENES AND OTHER A-FUSED PHENANTHRENES BY A PALLADIUM(O) COUPLING ELECTROCYCLIC RING-CLOSURE SEQUENCE [J].

GILCHRIST, TL ;

SUMMERSELL, RJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (09) :2595-2601

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