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

页码：273 / 283

页数：11

共 21 条

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