RE-FUNCTIONALIZATION OF ALPHA-SUBSTITUTED ISOCOLCHICIDES VIA NUCLEOPHILIC TELE-SUBSTITUTION

被引:9
作者
CAVAZZA, M [1 ]
PIETRA, F [1 ]
机构
[1] UNIV TRENT,IST CHIM,I-38050 TRENT,ITALY
关键词
D O I
10.1039/c39940000897
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
9-Methoxyisocolchicide 1 in excess methanethiolate-methanol, or Me2SO, slowly undergoes ipso-substitution giving 9-methylthioisocolchicide 3, which then suffers tele-substitution giving 11-methylthioisocolchicide 2; this activation by dicoordinated sulfur is used for amino re-functionalisation of the isocolchicide system.
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页码:897 / 898
页数:2
相关论文
共 12 条
[1]   THIO-ANALOGS OF MEISENHEIMER COMPLEXES/S [J].
BIGGI, G ;
PIETRA, F .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1973, (07) :229-230
[2]   NORMAL VS ABNORMAL NUCLEOPHILIC SUBSTITUTIONS ON CYCLOHEPTATRIENONES CARRYING A MOBILE ALPHA SUBSTITUENT - RATIONALIZATION [J].
BIGGI, G ;
DELCIMA, F ;
PIETRA, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (21) :7101-7107
[3]   REACTIONS OF ALKANEDITHIOLS WITH PICRYL HALIDES [J].
CABRINO, R ;
FARINA, E ;
DELCIMA, F ;
PIETRA, F .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (20) :2214-2216
[4]   COVALENT REVERSIBLE BINDING OF ALKOXIDES OR THIOLATES TO COLCHICINOIDS [J].
CAVAZZA, M ;
VERACINI, CA ;
PIETRA, F .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1992, (12) :2201-2204
[5]  
CAVAZZA M, 1978, TETRAHEDRON LETT, P2593
[6]  
CAVAZZA M, 1980, TETRAHEDRON LETT, P3703
[7]   THE STRUCTURE ELUCIDATION OF PSEUDOTHIOCOLCHICINE [J].
DANIELI, B ;
LESMA, G ;
PALMISANO, G ;
RIVA, R .
HELVETICA CHIMICA ACTA, 1985, 68 (08) :2173-2176
[8]   STABLE THIO-ANALOG OF A MEISENHEIMER COMPLEX VIA A SPIROANNELATION ROUTE - REQUIREMENTS FOR ANNEALATING CHAIN-LENGTH [J].
FARINA, E ;
VERACINI, CA ;
PIETRA, F .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1974, (16) :672-673
[9]   REVIVAL OF TROPONOID CHEMISTRY [J].
PIETRA, F .
ACCOUNTS OF CHEMICAL RESEARCH, 1979, 12 (04) :132-138
[10]   SYNTHESIS OF CHOLCHICINE [J].
SCHREIBER, J ;
LEIMGRUBER, W ;
PESARO, M ;
SCHUDEL, P ;
ESCHENMOSER, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1959, 71 (20) :637-640