RING-CHAIN TAUTOMERISM OF 3,5-DISUBSTITUTED 5,6,7,8-TETRAHYDRO-3H-[1,2,4]OXADIAZOLO[4,3-C]PYRIMIDINE, A NOVEL HETEROCYCLIC RING-SYSTEM

被引：13

作者：

KORBONITS, D ^{[1
]}

TOBIASHEJA, E ^{[1
]}

SIMON, K ^{[1
]}

KOLONITS, P ^{[1
]}

机构：

[1] TECH UNIV BUDAPEST,INST ORGAN CHEM,H-1521 BUDAPEST,HUNGARY

来源：

CHEMISCHE BERICHTE | 1991年 / 124卷 / 09期

关键词：

RING-CHAIN TAUTOMERISM; 3H-[1,2,4]-OXADIAZOLO[4,3-C]PYRIMIDINE, 5,6,7,8-TETRAHYDRO-;

D O I：

10.1002/cber.19911240931

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reaction of 3-aminopropionamide oxime (7) with two equiv. of benzaldehyde or of a substituted benzaldehyde gives cis-3,5-diaryl-5,6,7,8-tetrahydro-3H-[1,2,4]oxadiazolo[4,3-c]-pyrimidines (cis-11a-c,e). According to H-1-, C-13-, and N-15-NMR studies these compounds form in solution a novel triple tautomeric equilibrium comprising cis- and trans-11a-c, e and 3-[2-(benzylidineamino)ethyl]-5-aryl-4,5-dihydro-1,2,4-oxadiazoles (10a-c, e). However, the solid obtained from 7 and two equiv. of cinnamaldehyde proved to be an imine (10g), which again formed in solution a similar triple tautomeric system analogously to the mutarotation of sugars. The structure of 11a and 10g was confirmed by X-ray crystallography.

引用

页码：2065 / 2070

页数：6

共 15 条

[1] RULES FOR RING-CLOSURE
BALDWIN, JE
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) : 734 - 736
[2] CAPON B, 1969, CHEM REV, V69, P454
[3] GONCALVES H, 1964, CR HEBD ACAD SCI, V258, P3507
[4] GONCALVES H, 1967, B SOC CHIM FR, P2321
[5] GONCALVES H, 1970, B SOC CHIM FR, P2165
[6] RING CHAIN TAUTOMERISM OF 4-HYDROXIMINO-HEXAHYDROPYRIMIDINES SUBSTITUTED IN POSITION-2
KORBONITS, D
TOBIASHEJA, E
KOLONITS, P
[J]. CHEMISCHE BERICHTE, 1991, 124 (05) : 1199 - 1202
[7] RING TRANSFORMATION OF 1,2-DISUBSTITUTED 4(1H)-QUINAZOLONE OXIMES TO 3,5-DISUBSTITUTED 1,2,4-OXADIAZOLES
KORBONITS, D
KANZELSZVOBODA, I
GONCZI, C
SIMON, K
KOLONITS, P
[J]. CHEMISCHE BERICHTE, 1989, 122 (06) : 1107 - 1112
[8] CHEMISTRY OF THE HETEROCYCLIC PSEUDOBASIC AMINO-ALCOHOLS .38. RING-CHAIN TAUTOMERISM OF PYRIMIDO[6,1-A]ISOQUINOLINES
KORBONITS, D
HORVATH, G
KISS, P
SIMON, K
KOLONITS, P
[J]. CHEMISCHE BERICHTE, 1990, 123 (03) : 493 - 498
[9] A NEW TYPE OF DIMROTH REARRANGEMENT - FORMATION OF 1,2-DIHYDRO-3H-QUINAZOLONE 4-OXIMES FROM 4-AMINO-1,2-DIHYDROQUINAZOLINE 3-OXIDES
KORBONITS, D
KOLONITS, P
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (12): : 2163 - 2168
[10] A NOVEL RING TRANSFORMATION - 1,2,4-OXADIAZOLES FROM PYRIMIDINE-N-OXIDES
KORBONITS, D
SIMON, K
KOLONITS, P
[J]. TETRAHEDRON LETTERS, 1983, 24 (51) : 5763 - 5766

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