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

被引：3
|
作者：
HERMECZ, I
BREINING, T
SIMON, K
EROSTAKACSY, T
PODANYI, B
SESSI, J
机构：
[1] CHINOIN Pharmaceutical and Chemical Works Ltd., Budapest, H-1325
来源：
JOURNAL OF HETEROCYCLIC CHEMISTRY | 1991年 / 28卷 / 05期
关键词：
D O I：
10.1002/jhet.5570280536
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The acid-catalysed intramolecular nucleophilic addition of the phenyl ring to the C(9a) = N(1) double bond of ethyl 9-(N-methyl-N-phenyl)-4-oxotetrahydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylates, formed in the reactions of ethyl 9-bromo-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylates and N-methylaniline, gave the first examples of a new tetracyclic pyrimido[l',2':1,2]pyrido[3,2-b]indole ring system (7). X-ray diffraction analysis of 7a revealed that the annelation of the pyrimidine and piperidine rings is transoid, while that of the piperidine and pyrroline rings is cis, the piperidine ring adopts an unusual 6T8 twisted boat conformation, while the pyrroline ring has a 9T8a conformation.
引用
收藏
页码：1405 / 1411
页数：7
相关论文
共 50 条
  • [21] 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
  • [22] NITROGEN BRIDGEHEAD COMPOUNDS .48. SYNTHESIS AND STEREOCHEMISTRY OF 4-OXO-1,6,7,8,9,9A-HEXAHYDRO-4H-PYRIDO[1,2-A]PYRIMIDINE-3-CARBOXAMIDES
    HERMECZ, I
    KAJTAR, M
    SIMON, K
    BREINING, T
    SURJAN, PR
    TOTH, G
    MESZAROS, Z
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (16): : 2918 - 2925
  • [23] NITROGEN BRIDGEHEAD COMPOUNDS .37. STRUCTURAL STUDIES ON 9-HYDRAZONO-6,7,8,9-TETRAHYDRO-4-OXO-4H-PYRIDO[1,2-A]PYRIMIDINES BY H-1, C-13 AND N-15 NMR-SPECTROSCOPY
    TOTH, G
    SZOLLOSY, A
    ALMASY, A
    PODANYI, B
    HERMECZ, I
    BREINING, T
    MESZAROS, Z
    [J]. ORGANIC MAGNETIC RESONANCE, 1983, 21 (11): : 687 - 693
  • [24] 4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-[2-(2-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-3-yl)ethyl]piperidinium nitrate
    Sun, Yu
    Zhang, Huai-Hong
    [J]. ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 : 01647 - U3057
  • [25] Nitrogen bridgehead compounds. Part 92. Synthesis of 4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carboxamides, -3-acetamides and their tetrahydro derivatives
    Hermecz, I
    Vasvari-Debreczy, L
    Horvath, A
    Sipos, J
    Balogh, M
    Podanyi, B
    Kovacs, K
    [J]. ACH-MODELS IN CHEMISTRY, 1998, 135 (04): : 515 - 528
  • [26] 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
  • [27] Synthesis of 2-methyl-3-(2-(piperazin-1-yl)ethyl)-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one Derivatives as Antimicrobial Agents
    Krishnamurthy, Byregowda
    Vinaya, Kambappa
    Prasanna, Doddakunche S.
    Raghava, Byregowda
    Rangappa, Kanchugarakoppal S.
    [J]. LETTERS IN DRUG DESIGN & DISCOVERY, 2011, 8 (10) : 988 - 995
  • [28] Synthesis of 3-(2-chloroethyl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a] pyrimidin-4-one Derivatives as Antibacterial Agents
    Krishnamurthy, Byregowda
    Vinaya, Kambappa
    Rakshith, Devraj
    Prasanna, Doddakunche Shivaramu
    Rangappa, Kanchugarakoppal Subbegowda
    [J]. MEDICINAL CHEMISTRY, 2013, 9 (02) : 240 - 248
  • [29] Catalytic hydrogenation of 3-benzyloxycarbonylaminoazino[1,2-x]-azin-4-ones.: A facile access to 3-amino-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyridin-4-ones and 3-amino-6,7,8,9-tetrahydro-4H-azino[1,2-x]pyrimidin-4-ones
    Recnik, S
    Toplak, R
    Svete, J
    Pizzioli, L
    Stanovnik, B
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2000, 37 (04) : 783 - 790
  • [30] SEPARATION OF OPTICAL ISOMERS OF (+/)-3-CARBOXY-4-OXO-6-METHYL-6,7,8,9-TETRAHYDRO-4H-PYRIDO(1,2-ALPHA)PYRIMIDINE AND DL-THREO-1-(PARA-NITROPHENYL)-2-AMINO-PROPANEDIOL-1,3 BY MUTUAL-RESOLUTION .2. PREPARATION OF OPTICAL ISOMERS OF DL-THREO-1-(PARA-NITROPHENYL)-2-AMINO-PROPANEDIOL USING OPTICALLY-ACTIVE 3-CARBOXY-4-OXO-6-METHYL-6,7,8,9-TETRAHYDRO-4H-PYRIDO(1,2-ALPHA)PYRIMIDINEN
    FOGASSY, E
    ACS, M
    HERMECZ, I
    MATHE, I
    [J]. PERIODICA POLYTECHNICA-CHEMICAL ENGINEERING, 1977, 21 (02) : 229 - 235
12345