Studies with azoles and benzoazoles: A novel simple approach for synthesis of 3-functionally substituted 3-acylindoles

被引:41
作者
Abdel-Motaleb, Ramadan Maawad
Makhloof, Abdel-Moneim Abdel-Salam
Ibrahim, Hamada Mohamed
Elnagdi, Mohamed Hilmy [1 ]
机构
[1] Fayoum Univ, Dept Chem, Fac Sci, Al Fayyum, Egypt
[2] Cairo Univ, Fac Sci, Dept Chem, Giza, Egypt
关键词
D O I
10.1002/jhet.5570440119
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
3-Substituted acylindoles 8 are obtained via refluxing carboxylic acids with indole in acetic anhydride solutions. The formed 3-substituted acylindole 8a is readily converted into 4-aminopyrazol-3-ylindoles 20, and into 22. Indole reacts with chloroacetyl chloride to yield: 3-chloroacetylindole 9 which could also be utilized for synthesis of a number of 3-substituted indoles.
引用
收藏
页码:109 / 114
页数:6
相关论文
共 12 条
[1]  
Acheson RM, 1976, INTRO CHEM HETEROCYC
[2]   SYNTHESIS AND REACTIONS OF SOME 3-(2-HALOACYL)INDOLES [J].
BERGMAN, J ;
BACKVALL, JE ;
LINDSTRO.JO .
TETRAHEDRON, 1973, 29 (07) :971-976
[3]   ACYLATION OF THE ZINC SALT OF INDOLE [J].
BERGMAN, J ;
VENEMALM, L .
TETRAHEDRON, 1990, 46 (17) :6061-6066
[4]   MECHANISM OF DIAZO-COUPLING TO INDOLES AND EFFECT OF STERIC HINDRANCE ON RATE-LIMITING STEP [J].
CHALLIS, BC ;
RZEPA, HS .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1975, (11) :1209-1217
[5]   Studies on enaminonitriles: a new synthesis of 1,3-substituted pyrazole-4-carbonitrile [J].
Ghozlan, SAS ;
Abdelhamid, IA ;
Gaber, HM ;
Elnagdi, MH .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2005, 42 (06) :1185-1189
[6]  
Gilchrist T., 1998, HETEROCYCLIC CHEM
[7]   Acylation of indole under Friedel-Crafts conditions - An improved method to obtain 3-acylindoles regioselectively [J].
Ottoni, O ;
Neder, ADF ;
Dias, AKB ;
Cruz, RPA ;
Aquino, LB .
ORGANIC LETTERS, 2001, 3 (07) :1005-1007
[8]  
Oxford A. W., 1995, CONTEMP ORG SYNTH, V2, P35
[9]   Acylation, cyanoethylation and alkylation of methyl and phenyl indolylmagnesium salts:: Influence of the substituents on the C- and N-reaction products [J].
Rodríguez, JG ;
Urrutia, A .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1999, 36 (01) :129-135
[10]  
Slätt J, 2005, J HETEROCYCLIC CHEM, V42, P141