Synthesis of some novel alpha-cyanoketene S,S-acetals and their use in heterocyclic synthesis

被引:65
作者
Elgemeie, GH [1 ]
Elghandour, AH [1 ]
Elzanate, AM [1 ]
Ahmed, SA [1 ]
机构
[1] CAIRO UNIV,FAC SCI,DEPT CHEM,BENI SUEF BRANCH,BANI SUWAYF,EGYPT
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1997年 / 21期
关键词
D O I
10.1039/a702343j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A variety of novel alpha-cyanoketene S,S-acetals, readily prepared by the reaction of cyanoacetanilides or cyanothioacetamide with carbon disulfide, followed by alkylation, react smoothly with nucleophiles to afford variously substituted methylthio derivatives of pyrrole, pyrazole, pyridine and pyrimidine.
引用
收藏
页码:3285 / 3289
页数:5
相关论文
共 10 条
[1]  
ELGEMEIE GEH, 1994, LIEBIGS ANN CHEM, P955
[2]   NOVEL SYNTHESIS OF MERCAPTOPURINE AND PENTAAZA-AS-INDACENE ANALOGS - REACTION OF [BIS(METHYLTHIO)METHYLENE]MALONONITRILE AND ETHYL 2-CYANOO-3,3-BIS(METHYLTHIO)ACRYLATE WITH 5-AMINOPYRAZOLES [J].
ELGEMEIE, GEH ;
ELEZBAWY, SE ;
ALI, HA ;
MANSOUR, AK .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1994, 67 (03) :738-741
[3]   NUCLEOTIDES AND NUCLEOSIDES - DIRECT ROUTE TO CONDENSED PYRIDINETHIONE CARBOCYCLIC NUCLEOSIDES RELATED TO 3-DEAZAURIDINE [J].
ELGEMEIE, GEH ;
ATTIA, AME ;
FARAG, DS ;
SHERIF, SM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (10) :1285-1288
[4]   A CONVENIENT SYNTHESIS OF 5-DEAZA NONCLASSICAL ANTIFOLATES - REACTION OF CYANOTHIOACETAMIDE WITH SODIUM-SALTS OF 2-(HYDROXYMETHYLENE)-1-CYCLOALKANONES [J].
ELGEMEIE, GEH ;
HUSSAIN, BAW .
TETRAHEDRON, 1994, 50 (01) :199-204
[5]  
ELGEMEIE GEH, 1992, J CHEM SOC P1, P1037
[6]  
ELGEMEIE GEH, 1995, CARBOHYD RES, V268, P295
[7]  
Elgemeie GH, 1996, J CHEM RES-S, P340
[8]  
HSOMI A, 1990, J ORG CHEM, V55, P5308
[9]   ALPHA-OXOKETENE-S,S-ACETAL, N,S-ACETAL AND N,N-ACETAL - VERSATILE INTERMEDIATES IN ORGANIC-SYNTHESIS [J].
JUNJAPPA, H ;
ILA, H ;
ASOKAN, CV .
TETRAHEDRON, 1990, 46 (16) :5423-5506
[10]   THERMAL-REACTION OF BENZIMIDAZOLIUM N-ALLYLIDES [J].
MATSUDA, Y ;
YAMASHITA, M ;
TAKAHASHI, K ;
IDE, S ;
TORISU, K ;
FURUNO, K .
HETEROCYCLES, 1992, 33 (01) :295-302