GENERAL-METHODS FOR SYNTHESIZING 2,4-DIACYLPYRROLES AND THEIR PRECURSORS CONTAINING ONE OR 2 MASKED ACYL-GROUPS

被引:34
作者
CADAMURO, S [1 ]
DEGANI, I [1 ]
DUGHERA, S [1 ]
FOCHI, R [1 ]
GATTI, A [1 ]
PISCOPO, L [1 ]
机构
[1] UNIV TURIN,IST CHIM ORGAN,VIA P GIURIA 7,I-10125 TURIN,ITALY
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 02期
关键词
D O I
10.1039/p19930000273
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A thorough study of the synthesis of 2,4-diacylpyrroles by direct acylation of pyrrole and 2- and 3-acylpyrroles is reported. Among these, Friedel-Crafts acylation of 3-acylpyrroles is the most general and advantageous method because it utilises easily accessible starting materials. In addition it is always regiospecific and readily provides 2,4-diacylpyrroles containing identical or different acyl groups in very high yields (81-100%) under mild conditions. Alternative procedures concern the synthesis of precursors of 2,4-diacylpyrroles containing one or two acyl groups masked by a 1,3-benzodithiolyl or 1,3-benzoxathiolyl group and subsequent hydrolysis with HgO-35% aq. HBF4-Me2SO. Overall yields are always good (52-60%). Indirect acylation constitutes a secure complement to direct acylation when it is necessary to operate in the presence of protected acyl groups.
引用
收藏
页码:273 / 283
页数:11
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