Cycloaddition reactions of aldimines of 1,5-ketoaldehydes. Applications in the synthesis of polycyclic nitrogen heterocycles.

被引：18

作者：

Grigg, R ^{[1
]}

Thornton-Pett, M ^{[1
]}

Yoganathan, G ^{[1
]}

机构：

[1] Univ Leeds, Sch Chem, Mol Innovat Divers & Automated Synth MIDAS Ctr, Leeds LS2 9JT, W Yorkshire, England

来源：

TETRAHEDRON | 1999年 / 55卷 / 06期

关键词：

D O I：

10.1016/S0040-4020(98)01189-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aliphatic aldimines of a range of cyclic and acyclic 1,5-ketoaldehydes undergo metal catalysed regio- and stereo-specific imine --> azomethine ylide --> cycloaddition cascades. Acid catalysed cyclisations of the NH group of the pyrrolidine products onto the ketone functionality results in novel tri- and tetra-cyclic nitrogen heterocycles. (C) 1999 Elsevier Science Ltd. All rights reserved.

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页码：1763 / 1780

页数：18

相关论文

共 24 条

[1] SYNTHESIS BY A NOVEL CYCLIZATION REACTION AND CRYSTAL AND MOLECULAR-STRUCTURE OF 4-ETHYL-1-ISOPROPYL-3-[(PHENYLCARBAMOYL)METHYL]-3-PYRROLIN-2-ONE [J].

AUDISIO, G ;

PORZIO, W ;

ZETTA, L ;

FERRUTI, P .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1979, (10) :1391-1394

[2] ANALOGS OF TETRAHYDROFOLIC ACID .9. SYNTHESIS OF N-[1-(2-AMINO-4-HYDROXY-6-PHENYL-5-PYRIMIDYL)-3-PROPYL]-P-AMINOBENZOYL-L-GLUTAMIC ACID, A NONCLASSICAL INHIBITOR OF SOME FOLIC COFACTOR AREA ENZYMES [J].

BAKER, BR ;

SHAPIRO, HS .

JOURNAL OF MEDICINAL CHEMISTRY, 1963, 6 (06) :664-&

[3] X=Y-ZH COMPOUNDS AS POTENTIAL 1,3-DIPOLES .43. METAL-ION CATALYZED ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION REACTIONS OF IMINES AND MENTHYL ACRYLATE [J].

BARR, DA ;

DORRITY, MJ ;

GRIGG, R ;

HARGREAVES, S ;

MALONE, JF ;

MONTGOMERY, J ;

REDPATH, J ;

STEVENSON, P ;

THORNTONPETT, M .

TETRAHEDRON, 1995, 51 (01) :273-294

[4] CYANOHYDRIDOBORATE ANION AS A SELECTIVE REDUCING AGENT [J].

BORCH, RF ;

BERNSTEIN, MD ;

DURST, HD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (12) :2897-+

[5] CYCLIC POLYOLEFINS .11. CARBONYL-BRIDGED COMPOUNDS DERIVED FROM THE ADDUCT OF ALPHA-CARBETHOXYCYCLOHEXANONE AND ACROLEIN [J].

COPE, AC ;

SYNERHOLM, ME .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (11) :5228-5232

[6] CONVERSION OF KETONES HAVING DELTA,EPSILON-PI-FUNCTIONS TO CYCLOPENTANOLS BY ZINC-TRIMETHYLCHLOROSILANE [J].

COREY, EJ ;

PYNE, SG .

TETRAHEDRON LETTERS, 1983, 24 (28) :2821-2824

[7]

DALY JW, 1977, HELV CHIM ACTA, V60, P1128, DOI 10.1002/hlca.19770600336

[8] CHIRAL AUXILIARY MEDIATED CONJUGATE REDUCTION AND ASYMMETRIC PROTONATION - SYNTHESIS OF HIGH-AFFINITY LIGANDS FOR HIV PROTEASE INHIBITORS [J].

GHOSH, AK ;

LIU, WM .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (19) :6198-6201

[9]

GORDON AJ, 1972, CHEM COMPANION, P431

[10] X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .39. METALLO-AZOMETHINE YLIDES FROM ALIPHATIC ALDIMINES - FACILE REGIO-SPECIFIC AND STEREO-SPECIFIC CYCLOADDITION REACTIONS [J].

GRIGG, R ;

MONTGOMERY, J ;

SOMASUNDERAM, A .

TETRAHEDRON, 1992, 48 (47) :10431-10442