An improved coupling procedure for the Barton-Zard pyrrole synthesis

被引：13

作者：

Bobál, P ^{[1
]}

Lightner, DA ^{[1
]}

机构：

[1] Univ Nevada, Dept Chem, Reno, NV 89557 USA

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2001年 / 38卷 / 02期

关键词：

D O I：

10.1002/jhet.5570380239

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An improved final step in the Barton-Zard pyrrole synthesis uses inexpensive potassium carbonate as base in the coupling-cyclization reaction of vic-nitro-acetates with isocyanides. In this modification the isolated yields of synthetically useful 2-carboalkoxypyrroles (1a,b and 3) and 2-(p-toluenesulfonyl)pyrroles (2a,b) consistently rise to the 78-89% range. Conversion of 2a to 5-(p-toluenesulfonyl)-2-pyrrolinone 4 is conveniently and directly achieved by reaction with 30% hydrogen peroxide in acetic acid, thus circumventing the commonly used two step procedure involving bromination followed by solvolysis.

引用

收藏

页码：527 / 530

页数：4

相关论文

共 29 条

[1] SYNTHESIS OF PORPHYRINS DERIVED FROM CHLOROBIUM CHLOROPHYLLS [J].

ARCHIBALD, JL ;

WALKER, DM ;

SHAW, KB ;

MARKOVAC, A ;

MACDONALD, SF .

CANADIAN JOURNAL OF CHEMISTRY-BACK YEAR, 1966, 44 (03) :345-+

[2]

BARTON DHR, 1990, TETRAHEDRON, V46, P7587

[3] BIOSYNTHESIS OF PORPHYRINS AND RELATED MACROCYCLES .8. ENZYMIC DECARBOXYLATION OF UROPORPHYRINOGEN-III - STRUCTURE OF AN INTERMEDIATE, PHYRIAPORPHYRINOGEN-III, AND SYNTHESIS OF CORRESPONDING PORPHYRIN AND OF 2 ISOMERIC PORPHYRINS [J].

BATTERSBY, AR ;

HUNT, E ;

MCDONALD, E ;

PAINE, JB ;

SAUNDERS, J .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (09) :1008-1018

[4] A new convergent method for porphyrin synthesis based on a '3+1' condensation [J].

Boudif, A ;

Momenteau, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (11) :1235-1242

[5] A CONVENIENT PREPARATION OF BENZYL 4-(R1)-3-(R2)PYRROLE-2-CARBOXYLATES [J].

BURNS, DH ;

JABARA, CS ;

BURDEN, MW .

SYNTHETIC COMMUNICATIONS, 1995, 25 (03) :379-387

[6] Synthesis of a 10-oxo-bilirubin: Effects of the oxo group on conformation, transhepatic transport, and glucuronidation [J].

Chen, QQ ;

Huggins, MT ;

Lightner, DA ;

Norona, W ;

McDonagh, AF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (40) :9253-9264

[7] SYNTHESIS OF FACE TO FACE PORPHYRIN DIMERS LINKED BY 5,15-SUBSTITUENTS - POTENTIAL BINUCLEAR MULTIELECTRON REDOX CATALYSTS [J].

COLLMAN, JP ;

CHONG, AO ;

JAMESON, GB ;

OAKLEY, RT ;

ROSE, E ;

SCHMITTOU, ER ;

IBERS, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (03) :516-533

[8] PYRROLES AND RELATED COMPOUNDS .15. DIFFERENTIAL PROTECTION OF PYRROLE RINGS DURING PORPHYRIN SYNTHESIS - SYNTHESES OF MESOPORPHYRIN-XI [J].

CROOK, PJ ;

JACKSON, AH ;

KENNER, GW .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (03) :474-&

[9]

DOLPHIN D, 1979, PROPHYRINS

[10] SYNTHESIS OF BENZYL AND TERT-BUTYL 3-(2-METHOXYCARBONYLETHYL)-4-METHYLPYRROLE-2-CARBOXYLATES FROM METHYL 4-OXOBUTANOATE [J].

DRINAN, MA ;

LASH, TD .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1994, 31 (01) :255-257