SATURATED HETEROCYCLES .200. SYNTHESIS AND CONFORMATIONAL-ANALYSIS OF CONDENSED-SKELETON SATURATED 1,3-HETEROCYCLES

被引:0
作者
BERNATH, G
机构
来源
ACTA CHIMICA HUNGARICA-MODELS IN CHEMISTRY | 1992年 / 129卷 / 01期
关键词
D O I
暂无
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Transformations of versatile trifunctional synthons, 6,7-dialkoxy-1-[bis-(hydroxymethyl)methyl]-1,2,3,4-tetrahydroisoquinolines, furnished tetrahydroisoquinoline-fused azetidines and tetrahydroisoquinoline-fused 1,3-heterocycles (e.g. 1,3-oxazines, 1,3-oxazin-2-ones, 1,3-oxazin-4-ones, 1,3-thiazines, pyrimidinones and related 2-phenylimino-1,3-heterocycles). Conformational analysis of the above heterocycles by NMR and X-ray methods were performed. The ring-chain tautomerism of saturated fused-skeleton 1,3-oxazines, described by the equation log K(X) = (0.76 +/- 0.04) sigma+ + log K(X=H), is discussed. Ring closure reactions of 1-hydrazido- and 1-hydrazidomethyltetrahydroisoquinolines with aromatic aldehydes and ketones were performed and the relative configurations of the products were determined by means of DNOE measurements. The synthesis of a new family of the pyracridone group, 2-azapyracridones, is reported and an intermolecular hydrogen-transfer reaction is discussed. The synthesis of 1,3-heterocycles, e.g. 3-substituted and 2,3-disubstituted pyrimidin-4(3H)-ones, was achieved in retro Diels-Alder reactions. The unambigous synthetic pathway permitted the correction of erroneous structures in the earlier literature. A similar retro Diels-Alder process was developed for the synthesis of uracils and thiouracils. Bicyclic hetero derivatives, e.g. pyrimido[2,1-b]thiazine, were also prepared via retro Diels-Alder splitting.
引用
收藏
页码:107 / 157
页数:51
相关论文
共 121 条
[41]   RING CHAIN TAUTOMERISM IN 1,3-OXAZINES [J].
FULOP, F ;
PIHLAJA, K ;
MATTINEN, J ;
BERNATH, G .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (17) :3821-3825
[42]  
FULOP F, 1983, PHARMAZIE, V38, P218
[43]   SYNTHESIS OF PYRIMIDO[2,1-B]THIAZIN-6-ONE BY RETRO DIELS-ALDER REACTION [J].
FULOP, F ;
HUBER, I ;
SZABO, A ;
BERNATH, G ;
SOHAR, P .
TETRAHEDRON, 1991, 47 (36) :7673-7676
[44]   STEREOCHEMICAL STUDIES .87. SATURATED HETEROCYCLES .82. SYNTHESIS AND STERIC STRUCTURE OF STEREOISOMERIC N-SUBSTITUTED TETRAHYDRO-1,3-OXAZINES FUSED WITH NORBORNANE OR NORBORNENE [J].
FULOP, F ;
STAJER, G ;
BERNATH, G ;
SOHAR, P .
TETRAHEDRON, 1985, 41 (22) :5159-5168
[45]   STEREOCHEMICAL STUDIES .134. SATURATED HETEROCYCLES .138. SYNTHESIS AND STEREOCHEMISTRY OF STEREOISOMERIC 1,3-OXAZINO[4,3-ALPHA]ISOQUINOLINE AND 1,3-THIAZINO[4,3-ALPHA]ISOQUINOLINE [J].
FULOP, F ;
BERNATH, G ;
ELGHARIB, MS ;
KOBOR, J ;
SOHAR, P ;
PELCZER, I ;
ARGAY, G ;
KALMAN, A .
CHEMISCHE BERICHTE, 1990, 123 (04) :803-809
[46]   SYNTHESIS OF PARTIALLY SATURATED DIPYRIDO[1,2-A-4,3-D] PYRIMIDIN-11-ONES VIA CATALYTIC HYDROGEN-TRANSFER REACTION [J].
FULOP, F ;
HUBER, I ;
DOMBI, G ;
BERNATH, G .
TETRAHEDRON, 1987, 43 (06) :1157-1160
[47]   STEREOCHEMICAL STUDIES .136. SATURATED HETEROCYCLES .141. SYNTHESIS AND CONFORMATIONAL STUDY OF STEREOISOMERIC 2,2-DISUBSTITUTED-5,6-TRIMETHYLENE AND 2-DISUBSTITUTED-5,6-TETRAMETHYLENE-TETRAHYDRO-1,3-OXAZIN-4-ONES [J].
FULOP, F ;
PIHLAJA, K ;
MATTINEN, J ;
BERNATH, G .
TETRAHEDRON, 1987, 43 (20) :4565-4568
[48]   RING-CHAIN TAUTOMERISM IN 1,3-THIAZOLIDINES [J].
FULOP, F ;
MATTINEN, J ;
PIHLAJA, K .
TETRAHEDRON, 1990, 46 (18) :6545-6552
[49]  
FULOP F, 1988, ACTA CHIM HUNG, V125, P2193
[50]  
FULOP F, 1979, J HETEROCYCLIC CHEM, V19, P452