Synthesis of α-carbolines and β-carbolinones via intramolecular Diels-Alder reactions of 2(1H)-pyrazinones

被引：65

作者：

Tahri, A ^{[1
]}

Buysens, KJ ^{[1
]}

Van der Eycken, EV ^{[1
]}

Vandenberghe, DM ^{[1
]}

Hoornaert, GJ ^{[1
]}

机构：

[1] Katholieke Univ Leuven, Dept Chem, Organ Synth Lab, B-3001 Louvain, Belgium

来源：

TETRAHEDRON | 1998年 / 54卷 / 43期

关键词：

D O I：

10.1016/S0040-4020(98)00802-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2(1H)-Pyrazinones bearing a X-(o-C6H4)-C=C-R moiety (X=NH, NAc) are shown to undergo an intramolecular cycloaddition-elimination reaction on thermolysis in refluxing bromobenzene yielding alpha-caarbolines or beta-carbolinones. The product distribution depends strongly on the substitution pattern of the pyrazinone precursors and the solvent used for thermolysis. A high yield and selective formation of beta-carbolinones is possible when heating in tetrahydronaphthalene at reflux. Use of acetic anhydride as solvent facilitated the reaction and made it possible to realise a carbolin(on)e unaccessible by thermolysis in the previously mentioned solvents. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：13211 / 13226

页数：16

共 33 条

[1]

BANSAL RK, 1988, INDIAN J CHEM B, V27, P366

[2] INTRAMOLECULAR INVERSE ELECTRON DEMAND DIELS-ALDER REACTIONS OF PYRAZINES [J].

BIEDRZYCKI, M ;

DEBIE, DA ;

VANDERPLAS, HC .

TETRAHEDRON, 1989, 45 (19) :6211-6220

[3] (PLUS-OR-MINUS)11-AMINO-2,6-DIMETHYL-1,2,3,4-TETRAHYDRO-6H-QUININDOLIN-1-ONE, A NOVEL GABA(A) MODULATOR WITH POTENTIAL ANXIOLYTIC ACTIVITY [J].

BLACKBURN, TP ;

BOLTON, D ;

FORBES, IT ;

JOHNSON, CN ;

MARTIN, RT ;

THOMAS, DR ;

THOMPSON, M ;

UPTON, N .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (02) :279-284

[4]

BUYSENS KJ, 1995, TETRAHEDRON, V51, P12463

[5] Synthesis of new pyrrolo[3,4-b]- and [3,4-c]pyridin(on)es and related 1,7-naphthyridinones and 2,7-naphthyridines via intramolecular Diels-Alder reactions of 2(1H)-pyrazinones [J].

Buysens, KJ ;

Vandenberghe, DM ;

Hoornaert, GJ .

TETRAHEDRON, 1996, 52 (27) :9161-9178

[6]

DEBIE DA, 1988, TETRAHEDRON, V44, P2977

[7] SYNTHESES OF FUNCTIONALIZED PYRIDO[2,3-B]INDOLES [J].

FORBES, IT ;

JOHNSON, CN ;

THOMPSON, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (02) :275-281

[8] INTRAMOLECULAR DIELS-ALDER REACTIONS OF 2-(ALKYNYL)PYRIMIDINES AND 2-(ALKYNYL)PYRIDINES [J].

FRISSEN, AE ;

MARCELIS, ATM ;

GEURTSEN, G ;

DEBIE, DA ;

VANDERPLAS, HC .

TETRAHEDRON, 1989, 45 (16) :5151-5162

[9] RING-TRANSFORMATIONS OF PYRIMIDINES BY INTRAMOLECULAR DIELS-ALDER REACTIONS - SYNTHESIS OF ANNELATED PYRIDINES [J].

FRISSEN, AE ;

MARCELIS, ATM ;

VANDERPLAS, HC .

TETRAHEDRON, 1989, 45 (03) :803-812

[10] THE EFFECTS OF MEPROBAMATE, BARBITURATES, D-AMPHETAMINE AND PROMAZINE ON EXPERIMENTALLY INDUCED CONFLICT IN THE RAT [J].

GELLER, I ;

SEIFTER, J .

PSYCHOPHARMACOLOGIA, 1960, 1 (06) :482-492

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