NITROGEN BRIDGEHEAD COMPOUNDS .81. SYNTHESIS OF 9-(BENZYLIDENEHYDRAZONO)-6-METHYL-4-OXO-6,7,8,9-TETRAHYDRO-4H-PYRIDO[1,2-A-]PYRIMIDINE-3-CARBOXYLATES AND 9-(BENZYLIDENEHYDRAZINE)-6-METHYL-4-OXO-6,7-DIHYDRO-4H-PYRIDO[1,2-A]-PYRIMIDINE-3-CARBOXYLATES

被引：4

作者：

HERMECZ, I ^{[1
]}

BREINING, T ^{[1
]}

SESSI, J ^{[1
]}

PODANYI, B ^{[1
]}

机构：

[1] CHINOIN CHEM & PHARMACEUT WORKS LTD, H-1325 BUDAPEST, HUNGARY

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 1991年 / 28卷 / 03期

关键词：

D O I：

10.1002/jhet.5570280340

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of ethyl 9-hydrazono-6-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylate and benzaldehyde and its derivatives give a tautomeric mixture of 9-arylidenehydrazono-6,7,8,9-tetrahydro-and 9-arylidenehydrazine-6,7-dihydropyrido[1,2-a]pyrimidine derivatives. In the same case the enhydrazine and hydrazone tautomers were separated. The structure of the products were characterised by uv, ir, H-1 and C-13 nmr. The equilibrium of the tautomers was affected by the substituent of the phenyl ring. A fair linear correlation exists between the logarithms of the equilibrium constants and Hammett sigma(m) and sigma- constants of the substituents present on the phenyl ring.

引用

页码：781 / 785

页数：5

共 50 条

[1] NITROGEN BRIDGEHEAD COMPOUNDS .76. SYNTHESIS AND STEREOCHEMISTRY OF ETHYL 9-BENZYLIDENE-6,7,8,9-TETRAHYDRO-2-OXO-2H-PYRIDO[1,2-A]PYRIMIDINE-3-CARBOXYLATES AND 4-OXO-4H-PYRIDO[1,2-A]PYRIMIDINE-3-CARBOXYLATES AND THEIR HOMOLOGS
SIPOS, J
PODANYI, B
HERMECZ, I
PUSZTAY, L
TOTH, G
SZILAGYI, L
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1989, 26 (04) : 1061 - 1068
[2] NITROGEN BRIDGEHEAD COMPOUNDS .46. SYNTHESIS AND STEREOCHEMISTRY OF 9-FORMYL-6,7,9-TETRAHYDRO-2-OXO-2H-PYRIDO[1,2-A]PYRIMIDINE-3-CARBOXYLATES AND 4-OXO-4H-PYRIDO[1,2-A]PYRIMIDINE-3-CARBOXYLATES AND THEIR HOMOLOGS
HERMECZ, I
HORVATH, A
MESZAROS, Z
PONGORCSAKVARI, M
TOTH, G
SZOLLOSY, A
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1985, (12): : 1873 - 1879
[3] NITROGEN BRIDGEHEAD COMPOUNDS .82. AN UNEXPECTED RING TRANSFORMATION OF 6-HYDRAZONO-4-OXO-6,7,8,9-TETRAHYDRO-4H-PYRIDO[1,2-A]PYRIMIDINE-3-CARBOXYLATES
HERMECZ, I
HORVATH, A
EROSTAKACSY, T
PODANYI, B
[J]. HETEROCYCLES, 1991, 32 (08) : 1455 - 1460
[4] NITROGEN BRIDGEHEAD COMPOUNDS .80. UNUSUAL REACTION OF ETHYL 9-BROMO-4-OXO-6,7,8,9-TETRAHYDRO-4H-PYRIDO[1,2-A]PYRIMIDINE-3-CARBOXYLATES AND N-METHYLANILINE
HERMECZ, I
BREINING, T
SIMON, K
EROSTAKACSY, T
PODANYI, B
SESSI, J
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1991, 28 (05) : 1405 - 1411
[5] NITROGEN BRIDGEHEAD COMPOUNDS .29. TAUTOMERISM AND Z-E ISOMERISM OF ETHYL 9-AMINOMETHYLENE-4-OXO-6,7,8,9-TETRAHYDRO-4H-PYRIDO[1,2-A]PYRIMIDINE-3-CARBOXYLATES AND THEIR HOMOLOGS
TOTH, G
SZOLLOSY, A
PODANYI, B
HERMECZ, I
HORVATH, A
MESZAROS, Z
BITTER, I
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1983, (09): : 1409 - 1412
[6] NITROGEN BRIDGEHEAD COMPOUNDS .14. ACYLATION OF ETHYL 6-METHYL-4-OXO-6,7,8,9-TETRAHYDRO-PYRIDO(1,2-A)PYRIMIDINE-3-CARBOXILATE WITH ISOCYANATES
BITTER, I
HERMECZ, I
TOTH, G
DVORTSAK, P
BENDE, Z
MESZAROS, Z
[J]. TETRAHEDRON LETTERS, 1979, (52) : 5039 - 5040
[7] NITROGEN BRIDGEHEAD COMPOUNDS .12. REACTION OF THE ETHYL 6-METHYL-L-OXO-6,7,8,9-TETRAHYDRO-4H-PYRIDO[1,2-A]PYRIMIDINE-3-CARBOXYLATE WITH IMINIUM CHLORIDES
HERMECZ, I
BITTER, I
HORVATH, A
TOTH, G
MESZAROS, Z
[J]. TETRAHEDRON LETTERS, 1979, (27) : 2557 - 2558
[8] 4-hydroxy-2-quinolones. 120. Synthesis and structure of ethyl 2-hydroxy-4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxylates
Ukrainets, L. V.
Bereznyakova, N. L.
Petyunin, G. P.
Tugaibei, I. A.
Rybakov, V. B.
Chernyshev, V. V.
Turov, A. V.
[J]. KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2007, (06): : 864 - 876
[9] NITROGEN BRIDGEHEAD COMPOUNDS .83. SYNTHESIS AND RING TRANSFORMATION OF 6-METHYL-4-OXO-4H-PYRIDO[1,2-A]PYRIMIDINE-3-ACRYLATES
HERMECZ, I
HORVATH, A
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1992, 29 (02) : 559 - 564
[10] NITROGEN BRIDGEHEAD COMPOUNDS .43. FACILE SYNTHESIS OF N-SUBSTITUTED 6,7,8,9-TETRAHYDRO-4H-PYRIDO[1,2-A]-PYRIMIDINE-3-CARBOXAMIDES
BALOGH, M
HERMECZ, I
MESZAROS, Z
[J]. SYNTHESIS-STUTTGART, 1984, (07): : 582 - 586

← 1 2 3 4 5 →