Selenenylation-acylation of ketones with 2-chloroselenobenzoyl chloride.: A novel route to benzo[b]selenophenes

被引:22
作者
Kloc, K [1 ]
Mlochowski, J [1 ]
机构
[1] Wroclaw Univ Technol, Inst Organ Chem Biochem & Biotechnol, PL-50370 Wroclaw, Poland
关键词
ketones; selenenylation; acylation; benzo[b]selenophenes; 2-chloroselenobenzoyl chloride;
D O I
10.1016/S0040-4039(01)00839-5
中图分类号
O62 [有机化学];
学科分类号
070303 [有机化学]; 081704 [应用化学];
摘要
It has been found thar enolizable ketones and 1,3-diones react in neutral or basic medium with biselectrophiles such as 2-chloroselenobenzoyl chloride. The reaction takes place on the active alpha -methylene group. Selenenylation and subsequent acylation of the alpha -carbon atom take place and. depending on the ketone used, 3-hydroxybenzo[b]selenophenes or benzo[b]selenophen-3(2H)-ones are produced in moderate to high yields. (C) 2001 Published by Elsevier Science Ltd.
引用
收藏
页码:4899 / 4902
页数:4
相关论文
共 25 条
[1]
[Anonymous], COMPREHENSIVE HETERO
[2]
CHRISTIAENS LE, 1996, COMPREHENSIVE HETERO, V2, P731
[3]
DARI A, 1992, HETEROCYCLES, V34, P1737
[4]
THE BINARY REAGENT PHSECL-ZNCL2 - A POWERFUL CHLORO-PHENYLSELENENYLATING AGENT OF ELECTROPHILIC OLEFINS [J].
DONOFRIO, F ;
PARLANTI, L ;
PIANCATELLI, G .
TETRAHEDRON LETTERS, 1995, 36 (11) :1929-1932
[5]
Kloc K, 1989, LIEBIGS ANN CHEM, V54, P811
[6]
Aromatic compounds which contain selenium. [J].
Lesser, R ;
Weiss, R .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1924, 57 :1077-1082
[7]
The "selenium-indigo" (bis-selenium naphthene indigo) and aromatic compounds containing selenium. I. [J].
Lesser, R ;
Weiss, R .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1912, 45 :1835-1841
[8]
Mlochowski J, 1996, LIEBIGS ANN, P1751
[9]
MLOCHOWSKI J, 1993, LIEBIGS ANN CHEM, P1239
[10]
PAQUETTE L, 1994, ENCY REAGENTS ORGANI, P259