Regiocontrolled synthesis of pyrrole-2-carboxaldehydes and 3-pyrrolin-2-ones from pyrrole Weinreb amides

被引：49

作者：

Coffin, Aaron R. ^{[1
]}

Roussell, Michael A. ^{[1
]}

Tserlin, Elina ^{[1
]}

Pelkey, Erin T. ^{[1
]}

机构：

[1] Hobart & William Smith Coll, Dept Chem, Geneva, NY 14456 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 17期

关键词：

D O I：

10.1021/jo061043m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A regiocontrolled synthesis of 3,4-disubstituted pyrrole-2carboxaldehydes was completed in two steps from acyclic starting materials. A Barton-Zard pyrrole synthesis between N-methoxy-N-methyl-2-isocyanoacetamide and R-nitroalkenes or,-nitroacetates provided N-methoxy-N-methyl pyrrole-2-carboxamides ( pyrrole Weinreb amides), which were converted into the corresponding pyrrole-2-carboxaldehydes by treatment with lithium aluminum hydride. A regioselective oxidation of the pyrrole-2-carboxaldehydes gave the corresponding 3,4-disubstituted 3-pyrrolin-2-ones.

引用

页码：6678 / 6681

页数：4

共 64 条

[1] A new synthesis of porphobilinogen analogues, inhibitors of hydroxymethylbilane synthase [J].

Ahmed, R ;

Leeper, FJ .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (01) :21-23

[2]

Bai AP, 2001, CHINESE CHEM LETT, V12, P775

[3] Rational synthesis of β-substituted chlorin building blocks [J].

Balasubramanian, T ;

Strachan, JP ;

Boyle, PD ;

Lindsey, JS .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (23) :7919-7929

[4] The first conversion of primary alkyl halides to nitroalkanes under aqueous medium [J].

Ballini, R ;

Barboni, L ;

Giarlo, G .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (20) :6907-6908

[5] CHEMOSELECTIVE SYNTHESIS OF FUNCTIONALIZED CONJUGATED NITROALKENES [J].

BALLINI, R ;

CASTAGNANI, R ;

PETRINI, M .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07) :2160-2162

[6] A mild, one-pot method for the conversion of carboxylic acids into the corresponding Weinreb amides [J].

Banwell, M ;

Smith, J .

SYNTHETIC COMMUNICATIONS, 2001, 31 (13) :2011-2019

[7] New insights into the synthesis of porphyrin-corrole and biscorrole systems [J].

Barbe, JM ;

Burdet, F ;

Espinosa, E ;

Gros, CP ;

Guilard, R .

JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, 2003, 7 (4-5) :365-374

[8]

BARTON DHR, 1990, TETRAHEDRON, V46, P7587

[9] A new synthesis of staurosporinone [J].

Beccalli, EM ;

Gelmi, ML ;

Marchesini, A .

TETRAHEDRON, 1998, 54 (24) :6909-6918

[10] DIASTEREOSELECTIVE SYNTHESIS OF PHYCOCYANOBILIN CYSTEINE ADDUCTS [J].

BISHOP, JE ;

NAGY, JO ;

OCONNELL, JF ;

RAPOPORT, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (21) :8024-8035

← 1 2 3 4 5 6 7 →