SYNTHESIS OF A NEW 1,4-DIHYDROPYRIDINE CONTAINING THE IMIDAZO[1,5-A]PYRIDINE NUCLEUS

被引:9
作者
FOS, E
BOSCA, F
MAULEON, D
CARGANICO, G
机构
[1] Laboratories Menarini S.A, Badalona
[2] Universidad Politécnica de Valencia, Valencia, Camino de Vera
关键词
D O I
10.1002/jhet.5570300232
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of the new dihydropyridine diethyl 1,4-dihydro-4-(imidazo[1,5-a]pyridin-8-yl)-2,6-dimethyl-pyridine-3,5-dicarboxylate (1) is described. After many attempts to prepare the key intermediate aldehyde 2a by different approaches, this compound has been obtained in good yields from methyl 2-cyano-3-pyridinecarboxylate (10). A three-step procedure involving reduction to the amine, formylation with concomitant cyclization and reduction of the ester group was used.
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页码:473 / 476
页数:4
相关论文
共 16 条
  • [1] DESIGN OF AN ANTITHROMBOTIC ANTIHYPERTENSIVE AGENT (WY-27569) - SYNTHESIS AND EVALUATION OF A SERIES OF 2-HETEROARYL-SUBSTITUTED DIHYDROPYRIDINES
    ARCHIBALD, JL
    BRADLEY, G
    OPALKO, A
    WARD, TJ
    WHITE, JC
    ENNIS, C
    SHEPPERSON, NB
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (02) : 646 - 652
  • [2] HETEROCYCLIC SYSTEMS RELATED TO PYRROCOLINE .1. 2-3A-DIAZAINDENE
    BOWER, JD
    RAMAGE, GR
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1955, : 2834 - 2837
  • [3] CYANATION OF AMINE OXIDE SALTS - A NEW SYNTHESIS OF CYANOPYRIDINES
    FEELY, WE
    BEAVERS, EM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (15) : 4004 - 4007
  • [4] FIFE WK, 1984, HETEROCYCLES, V22, P93
  • [5] FIFE WK, 1984, HETEROCYCLES, V22, P1121
  • [6] IMIDAZO[1,5-A]PYRIDINES - A NEW CLASS OF THROMBOXANE-A2 SYNTHETASE INHIBITORS
    FORD, NF
    BROWNE, LJ
    CAMPBELL, T
    GEMENDEN, C
    GOLDSTEIN, R
    GUDE, C
    WASLEY, JWF
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1985, 28 (02) : 164 - 170
  • [7] FURUKAWA S, 1955, J PHARM SOC JAPAN, V3, P232
  • [8] OXIMES OF THE PYRIDINE SERIES
    GINSBURG, S
    WILSON, IB
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (02) : 481 - 485
  • [9] FORMYLATION OF AMINES
    HUFFMAN, CW
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1958, 23 (05) : 727 - 729
  • [10] NEW DEVELOPMENTS IN CA-2+ CHANNEL ANTAGONISTS
    JANIS, RA
    TRIGGLE, DJ
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (06) : 775 - 785