SYNTHESIS OF THE 6 ISOMERIC THIENO[C]-FUSED 1,5-NAPHYTHYRIDINES AND 1,6-NAPHTHYRIDINES

被引:22
作者
GRONOWITZ, S
MALM, J
HORNFELDT, AB
机构
关键词
D O I
10.1135/cccc19912340
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Through the use of Pd(0)-catalyzed coupling between 2- and 4-formyl-3-thiopheneboronic acids and 3-amino-2-bromopyridine and 4-acetamido-3-bromopyridine, convenient one-pot procedures for the preparation of thieno[2,3-c]-1,5-naphthyridine, thieno[3,4-c]-1,5-naphthyridine, thieno[2,3-c]-1,6-naphthyridine, and thieno[3,4-c]-1,6-naphthyridine have been developed. In order to obtain thieno[3,2-c]-1,6-naphthyridine 2-(tributylstannyl)-3-thiophene aldehyde had to be used, since the organometallic partner in the coupling reaction, 3-formyl-2-thiopheneboronic acid, is too easily deboronated. The effect of silver(I) oxide and thallium(I) carbonate on the coupling was studied. H-1 and C-13 NMR spectra of the six isomeric thieno[c]-fused 1,5- and 1,6-naphthyridines are discussed.
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页码:2340 / 2351
页数:12
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共 37 条
  • [1] Coulson DR, 1971, INORG SYN, V13, P121, DOI DOI 10.1002/9780470132449.CH23
  • [2] ELECTRONIC-SPECTRA OF DITHIENO ANALOGS OF PHENANTHRENE
    DAHLGREN, T
    GLANS, J
    GRONOWITZ, S
    DAVIDSSON, A
    NORDEN, B
    PEDERSEN, PB
    THULSTRUP, EW
    [J]. CHEMICAL PHYSICS, 1979, 40 (03) : 397 - 404
  • [3] ELOY F, 1970, B SOC CHIM BELG, V79, P301
  • [4] ADDITION OF ARYL HALIDES TO TETRAKIS(TRIPHENYLPHOSPHINE)PALLADIUM(0)
    FITTON, P
    RICK, EA
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1971, 28 (02) : 287 - &
  • [5] BROMINATION OF 3-AMINO-PYRIDINE AND 3-DIMETHYLAMINO-PYRIDINE
    FOX, GJ
    HEPWORTH, JD
    HALLAS, G
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (01): : 68 - 69
  • [6] NEW HETEROAROMATIC SYSTEMS DERIVED FROM O-FORMYLTHIOPHENEBORONIC ACIDS
    GRONOWIT.S
    BUGGE, A
    [J]. ACTA CHEMICA SCANDINAVICA, 1965, 19 (06): : 1271 - &
  • [7] GRONOWITZ S, 1988, CHEM SCRIPTA, V28, P281
  • [8] GRONOWITZ S, 1977, CHEM SCRIPTA, V12, P57
  • [9] GRONOWITZ S, 1986, CHEM SCRIPTA, V26, P311
  • [10] GRONOWITZ S, 1986, CROAT CHEM ACTA, V59, P313