Unexpected and facile bridgehead substitution in 5,6,7,8,9,10-hexahydro-5,9-methanopyrimido[4,5-b]azocin-4(3H)-ones

被引：5

作者：

Taylor, EC ^{[1
]}

Dowling, JE ^{[1
]}

Schrader, T ^{[1
]}

Bhatia, B ^{[1
]}

机构：

[1] Princeton Univ, Dept Chem, Princeton, NJ 08544 USA

来源：

TETRAHEDRON | 1998年 / 54卷 / 33期

关键词：

D O I：

10.1016/S0040-4020(98)00512-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Condensation of 2,6-diamino-4(3 (H) under bar)-pyrimidinone with 2-cyclohexen-1-one gives a tricyclic product resulting from Michael addition followed by intramolecular hemiaminal formation. A methodology has been developed for reductive removal of the bridgehead hydroxyl group. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：9507 / 9518

页数：12

相关论文

共 24 条

[1] REGIOSELECTIVE SYNTHESIS OF PYRIDO[2,3-D]PYRIMIDINES [J].

ANDERSON, GL .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1985, 22 (05) :1469-1470

[2]

[Anonymous], CHEM COMMUN

[3] REGIOSELECTIVE BEHAVIOR OF UNSATURATED KETO ESTERS TOWARD VINYLOGOUS AMIDES [J].

BENNETT, GB ;

MASON, RB .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (11) :1919-1922

[4] PYRIDO[2,3-D]PYRIMIDINES .4. SYNTHETIC STUDIES LEADING TO VARIOUS OXOPYRIDO[2,3-D]PYRIMIDINES [J].

BROOM, AD ;

SHIM, JL ;

ANDERSON, GL .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (07) :1095-1099

[5] IMPROVED SYNTHESES IN THE PYRIMIDINE SERIES .1. THE USE OF PYRIMIDINE-THIOLS [J].

BROWN, DJ .

JOURNAL OF THE SOCIETY OF CHEMICAL INDUSTRY-LONDON, 1950, 69 (12) :353-356

[6] REACTIONS BETWEEN ENAMINONES AND ENONES .2. C VERSUS N-ALKYLATION WITH CYCLOHEX-2-ENONE - STRUCTURE CONFIRMATION BY REDUCTION OF A DIENAMINONE DERIVATIVE OF DEHYDRATED DIMEDONE DIMER [J].

CHAABAN, I ;

GREENHILL, JV ;

RAMLI, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (12) :3120-3124

[7] A STUDY OF CHEMICAL CARCINOGENESIS .104. A STUDY OF REACTIONS OF ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS WITH DEOXYGUANOSINE [J].

CHUNG, FL ;

ROY, KR ;

HECHT, SS .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (01) :14-17

[8] SOME NEW SYNTHESES OF AMINO- AND ALKYLAMINOPYRIMIDINES AND -PTERIDINES [J].

CURRAN, WV ;

ANGIER, RB .

JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (10) :2672-&

[9] MODERN METHODS FOR THE RADICAL DEOXYGENATION OF ALCOHOLS [J].

HARTWIG, W .

TETRAHEDRON, 1983, 39 (16) :2609-2645

[10] O-ALLYL PROTECTION OF GUANINE AND THYMINE RESIDUES IN OLIGODEOXYRIBONUCLEOTIDES [J].

HAYAKAWA, Y ;

HIROSE, M ;

NOYORI, R .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (20) :5551-5555