An efficient route to trans-4,5-dihydrothiophenes and thiazoles via nitrogen and sulfur ylides

被引：15

作者：

Dawood, KM ^{[1
]}

机构：

[1] Cairo Univ, Fac Sci, Dept Chem, Giza 12613, Egypt

来源：

SYNTHETIC COMMUNICATIONS | 2001年 / 31卷 / 11期

关键词：

D O I：

10.1081/SCC-100103983

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A number of versatile sulfonium and pyridinium salts reacted stereoselectively with some arylidenecyanothioacetamides under mild heating to give trans-4,5-dihydrothiophenes. The stereochemistry of the products was established on the basis of X-ray analysis. Repeating the same reactions at high temperature furnished a mixture of trans-4,5-dihydrothiophenes and thiazoles.

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页码：1647 / 1658

页数：12

相关论文

共 15 条

[1] DIMERIZATION OF 3-ARYL-2-CYANOTHIOACRYLAMIDES - [2S + 4S] CYCLOADDITION TO GIVE SUBSTITUTED 3,4-DIHYDRO-2H-THIOPYRANS [J].

BRUNSKILL, JSA ;

DE, A ;

EWING, DF .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1978, (06) :629-633

[2] Synthesis and biological activity of novel 1H,3H-thiazolo[3,4-a] benzimidazoles:: non-nucleoside human immunodeficiency virus type 1 reverse transcriptase inhibitors [J].

Chimirri, A ;

Grasso, S ;

Monforte, P ;

Rao, A ;

Zappalà, M ;

Monforte, AM ;

Pannecouque, C ;

Witvrouw, M ;

Balzarini, J ;

De Clercq, E .

ANTIVIRAL CHEMISTRY & CHEMOTHERAPY, 1999, 10 (04) :211-217

[3]

ELDEBESS TMA, 1977, THESIS CAIRO U

[4] PYRIMIDINE-DERIVATIVES AND RELATED COMPOUNDS .4. ROUTE FOR SYNTHESIS OF PYRAZOLO[3,4-E]-AS-TRIAZINES, PYRAZOLO[3,4-D]PYRIMIDINES, AND PYRAZOLO[1,5-C]-AS-TRIAZINES [J].

ELNAGDI, MH ;

ELMOGHAYAR, MRH ;

FLEITA, DH ;

HAFEZ, EAA ;

FAHMY, SM .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (24) :3781-3784

[5] Structure-activity relationships of anti-HIV-1 N-alkoxy- and N-allyloxy-benzimidazoles [J].

Evans, TM ;

Gardiner, JM ;

Mahmood, N ;

Smis, M .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (04) :409-412

[6]

Farag AM, 1997, HETEROATOM CHEM, V8, P45, DOI 10.1002/(SICI)1098-1071(1997)8:1<45::AID-HC6>3.0.CO

[7]

2-1

[8] Synthesis and reactivity of benzothiazol-2-ylcarbonylhydroximoyl chloride, a versatile synthon [J].

Farag, AM ;

Dawood, KM ;

Abdelhamid, AO .

TETRAHEDRON, 1997, 53 (51) :17461-17468

[9]

Ramaiah K, 1999, INDIAN J CHEM B, V38, P302

[10] Synthesis and biological activity of novel nonnucleoside inhibitors of HIV-1 reverse transcriptase. 2-aryl-substituted benzimidazoles [J].

Roth, T ;

Morningstar, ML ;

Boyer, PL ;

Hughes, SH ;

Buckheit, RW ;

Michejda, CJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (26) :4199-4207