An efficient and general strategy for the synthesis of 4-phosphorylated pyrazoles from beta-hydrazono phosphine oxides.

被引:44
作者
Palacios, F
Aparicio, D
delosSantos, JM
机构
[1] Depto. de Quim. Orgánica, Facultad de Farmacia, Universidad del País Vasco, 01080 Vitoria
关键词
D O I
10.1016/S0040-4020(96)00073-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple and efficient synthesis of aminopyrazoles substituted with a phosphino oxide and sulphide groups in the 4-position 1 is described. The key step is a regioselective addition of lithiated beta-hydrazonophosphine oxides 2 to isocyanates and isothiocyanates to give functionalized amides 3 and 7. Subsequent cyclization of 3 with phosphorus oxychloride in the presence of triethylamine afforded pyrazoles derived from phosphine oxides 1 and phosphine sulphides 8. Substituted heterocycles 1 can also be obtained in ''one pot'' reaction from phosphine oxides 2 when these compounds are metallated followed by addition of isocyanates and phosphorus oxychloride.
引用
收藏
页码:4123 / 4132
页数:10
相关论文
共 50 条
  • [21] ENDERS D, 1983, LIEBIGS ANN CHEM, P1439
  • [22] ASYMMETRIC MICHAEL ADDITIONS VIA SAMP-/RAMP-HYDRAZONES ENANTIOSELECTIVE SYNTHESIS OF 2-SUBSTITUTED 4-OXOSULFONES
    ENDERS, D
    PAPADOPOULOS, K
    HERDTWECK, E
    [J]. TETRAHEDRON, 1993, 49 (09) : 1821 - 1830
  • [23] ENANTIOSELECTIVE SYNTHESIS AND DETERMINATION OF THE CONFIGURATION OF STENUSINE, THE SPREADING AGENT OF THE BEETLE STENUS-COMMA
    ENDERS, D
    TIEBES, J
    DEKIMPE, N
    KEPPENS, M
    STEVENS, C
    SMAGGHE, G
    BETZ, O
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (18) : 4881 - 4884
  • [24] Enders D., 1984, ASYMMETRIC SYNTHES B, V3, P275
  • [25] FEST C, 1994, Patent No. 4315384
  • [26] FODOR G, 1972, ANGEW CHEM, V84, P947
  • [27] 3-SUBSTITUTED PYRAZOLE DERIVATIVES AS INHIBITORS AND INACTIVATORS OF LIVER ALCOHOL-DEHYDROGENASE
    FRIES, RW
    BOHLKEN, DP
    PLAPP, BV
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1979, 22 (04) : 356 - 359
  • [28] GYSIN H, 1956, Patent No. 2754244
  • [29] HAFEZ EAA, 1984, HETEROCYCLES, V22, P1821
  • [30] THE SYNTHESIS OF RP-66471 - A POTENT POTASSIUM CHANNEL OPENER
    HART, TW
    GUILLOCHON, D
    PERRIER, G
    SHARP, BW
    TOFT, MP
    VACHER, B
    WALSH, RJA
    [J]. TETRAHEDRON LETTERS, 1992, 33 (47) : 7211 - 7214