AN IMPROVED SYNTHESIS OF PYRROLES FROM N-PARA-TOLUENESULFONYLGLYCINE ESTERS AND ALPHA,BETA-UNSATURATED ALDEHYDES AND KETONES

被引：31

作者：

LASH, TD

HOEHNER, MC

机构：

[1] Department of Chemistry, Illinois State University, Normal, Illinois

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 1991年 / 28卷 / 07期

关键词：

D O I：

10.1002/jhet.5570280705

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-p-Toluenesulfonylglycine esters 2 condensed with alpha,beta-unsaturated carbonyl compounds 1 in the presence of the non-nucleophilic base DBU to give hydroxypyrrolidines 3. Dehydration with phosphorus oxychloride-pyridine, followed by DBU mediated elimination of p-toluenesulfinic acid, gave a series of synthetically useful pyrrole-2-carboxylates 5.

引用

页码：1671 / 1676

页数：6

共 34 条

[1] C-13 NUCLEAR MAGNETIC-RESONANCE SPECTRA OF SOME SUBSTITUTED PYRROLES [J].

ABRAHAM, RJ ;

LAPPER, RD ;

SMITH, KM ;

UNSWORTH, JF ;

ROBINSON, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1974, (09) :1004-1009

[2]

Bailey D. M., 1971, ORG SYNTH, V51, P100

[3]

BARTON DHR, 1990, TETRAHEDRON, V46, P7587

[4] A NEW SYNTHESIS OF PYRROLES FROM NITROALKENES [J].

BARTON, DHR ;

ZARD, SZ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (16) :1098-1100

[5] Local anesthetics in the pyrrole series. I [J].

Blicke, FF ;

Blake, ES .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1930, 52 :235-240

[6]

BUDJIKIEWICZ H, 1964, J CHEM SOC, P1949

[7]

FISCHER H, 1926, Z PHYSL CHEM, V155, P58

[8]

FISCHER H, 1928, CHEM BER, V61, P1074

[9] SYNTHETIC AND BIOSYNTHETIC-STUDIES OF PORPHYRINS .2. SYNTHESIS OF ISOPEMPTO-PORPHYRINS AND ISOCHLOROCRUORO-PORPHYRINS [J].

GAMES, DE ;

JACKSON, AH ;

OHANLON, PJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (23) :2501-2505

[10]

GARIDO DOA, 1988, J ORG CHEM, V53, P403

← 1 2 3 4 →