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

[1] PYRROLE ACYLATION AND SPECTRAL STUDIES [J].

ANDERSON, AG ;

EXNER, MM .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (24) :3952-3955

[2] PYRROLE CHEMISTRY .28. SUBSTITUTION-REACTIONS OF 1-(PHENYLSULFONYL)PYRROLE AND SOME DERIVATIVES [J].

ANDERSON, HJ ;

LOADER, CE ;

XU, RX ;

LE, N ;

GOGAN, NJ ;

MCDONALD, R ;

EDWARDS, LG .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1985, 63 (04) :896-902

[3]

ANDERSON HJ, 1990, PYRROLES CHEM HETE 1, V48

[4]

BARBERO M, 1990, GAZZ CHIM ITAL, V120, P619

[5]

BARBERO M, 1986, SYNTHESIS-STUTTGART, P1074

[6]

BARBERO M, 1987, GAZZ CHIM ITAL, V117, P227

[7] PENTAATOMIC HETEROAROMATIC CATIONS .18. ACYLATION OF PYRROLE AND N-METHYLPYRROLE WITH 1,3-BENZOXATHIOLIUM TETRAFLUOROBORATES - A HIGH-YIELD METHOD FOR THE SYNTHESIS OF DIACYLPYRROLES [J].

BARBERO, M ;

CADAMURO, S ;

DEGANI, I ;

FOCHI, R ;

GATTI, A ;

REGONDI, V .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (10) :2245-2250

[8]

BELANGER P, 1979, TETRAHEDRON LETT, P2505

[9] PENTATOMIC HETEROAROMATIC CATIONS .10. NEW ROUTE FOR REDUCTION OF FUNCTIONAL-GROUP OF CARBOXYLIC-ACIDS, ACID-CHLORIDES, ANHYDRIDES, ESTERS, NITRILES, TRIHALOGENOMETHYL COMPOUNDS, ALDEHYDES, AND KETONES TO METHYL OR METHYLENE GROUPS [J].

DEGANI, I ;

FOCHI, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1978, (10) :1133-1136

[10]

DEGANI I, 1976, SYNTHESIS-STUTTGART, P759

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