TRANSFORMATIONS IN THE ISOXAZOLE SERIES - SYNTHESIS OF SUBSTITUTED 2-AMINOTHIAZOLES

被引：10

作者：

PASCUAL, A

机构：

[1] Agro Division, Ciba-Geigy AG, Basel

来源：

HELVETICA CHIMICA ACTA | 1991年 / 74卷 / 03期

关键词：

D O I：

10.1002/hlca.19910740309

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Substitued N-(isoxazol-4-yl)thioureas 1 undergo a transformation in the presence of hexacarbonylmolybdenum and acid to yield functionalized thiazoles 3 in a one-pot reaction. In a few cases, 1,4,5-trisubstituted dihydroimidazolethiones 4 are also isolated as side products. Mechanistic considerations are outlined and scope and limitations of this new methodology discussed.

引用

收藏

页码：531 / 542

页数：12

相关论文

共 34 条

[1]

AKHREM AA, 1989, ZH ORG KHIM+, V25, P2120

[2] BASE-INDUCED RING CLEAVAGE OF 4-FUNCTIONALIZED-3-UNSUBSTITUTED ISOXAZOLES - SYNTHESIS OF 5-AMINOAZOLES AND 4-CYANOAZOLES [J].

ALBEROLA, A ;

ANTOLIN, LF ;

GONZALEZ, AM ;

LAGUNA, MA ;

PULIDO, FJ .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1986, 23 (04) :1035-1038

[3]

ASSEF G, 1976, TETRAHEDRON LETT, V17, P3313

[4] A NEW NITRILE OXIDE BASED SYNTHESIS OF THE ANTITUMOR AGENT GEIPARVARIN [J].

BARALDI, PG ;

BARCO, A ;

BENETTI, S ;

GUARNERI, M ;

MANFREDINI, S ;

POLLINI, GP ;

SIMONI, D .

TETRAHEDRON LETTERS, 1985, 26 (43) :5319-5322

[5]

BARALDI PG, 1987, SYNTHESIS-STUTTGART, P857

[6] USE OF [3+2] CYCLOADDITION IN ELABORATION OF THE OMEGA-CHAIN OF PROSTAGLANDINS [J].

BARCO, A ;

BENETTI, S ;

BARALDI, PG ;

SIMONI, D ;

GUARNERI, M ;

GANDOLFI, C ;

POLLINI, GP .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (15) :3141-3142

[7]

BAUER VJ, 1968, J MED CHEM, V11, P984, DOI 10.1021/jm00311a016

[8] H-1-NMR AND C-13-NMR SPECTRA OF PHENYL-SUBSTITUTED AZOLE DERIVATIVES .2. CONFORMATIONAL STUDY [J].

BEGTRUP, M .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1974, B 28 (01) :61-77

[9] N'-SUBSTITUTED N-ACYL-THIOUREAS AND N-IMIDOYL-THIOUREAS - PREPARATION AND CONVERSION OF N',N'-DISUBSTITUTED COMPOUNDS INTO 2-(N,N-DISUBSTITUTED AMINO)THIAZOL-5-YL KETONES [J].

BRINDLEY, JC ;

CALDWELL, JM ;

MEAKINS, GD ;

PLACKETT, SJ ;

PRICE, SJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (05) :1153-1158

[10]

BUCHI G, 1972, J AM CHEM SOC, V94, P9128

← 1 2 3 4 →