Singlet oxygen oxidation of pyrroles: Synthesis and chemical transformations of novel 4,4-bis(trifluoromethyl)imidazoline analogs

被引：62

作者：

Li, HY ^{[1
]}

Drummond, S ^{[1
]}

DeLucca, I ^{[1
]}

Boswell, GA ^{[1
]}

机构：

[1] DUPONT MERCK PHARMACEUT CO,EXPT STN,DIV CHEM SCI,WILMINGTON,DE 19880

来源：

TETRAHEDRON | 1996年 / 52卷 / 34期

关键词：

pyrrole; imidazoline; singlet oxygen; oxidation; dehydrocyclization;

D O I：

10.1016/0040-4020(96)00578-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel singlet oxygen ring cleavage of pyrrole 5a and subsequent acid-catalyzed facile dehydrocyclization afforded a new series of 4,4-bis(trifluoromethyl)imidazolines with a p-fluorophenacyl side chain at the 5-position, which have shown potent acyl CoA: cholesterol acyltransferase (ACAT) and cholesterol biosynthesis inhibitory activities. Copyright (C) 1996 The DuPont Merck Pharmaceutical Company.

引用

页码：11153 / 11162

页数：10

共 14 条

[1] Novel 4,4-bis(trifluoromethyl) imidazolines as stereospecific and orally active Acyl CoA: Cholesterol acyltransferase (ACAT) inhibitors and antihypercholesterolemic agents [J].

Boswell, GA ;

Li, HY ;

Delucca, I ;

Billheimer, JT ;

Drummond, S ;

Gillies, PJ ;

Robinson, C .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (07) :885-888

[2] 1-(DIALKYLAMINO)ISOBENZOFURANS - GENERATION AND USE FOR ANNELATION OF AROMATIC RINGS [J].

CHEN, CW ;

BEAK, P .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (17) :3325-3334

[3] PYRROLE STUDIES .35. AERIAL OXIDATION OF 4-SUBSTITUTED 3-AMINO-2,5-DIMETHYLPYRROLES - AN X-RAY CRYSTALLOGRAPHIC AND SPECTROSCOPIC STUDY OF THE OXIDATION-PRODUCTS [J].

CIRRINCIONE, G ;

DATTOLO, G ;

ALMERICO, AM ;

AIELLO, E ;

JONES, RA ;

DAWES, HM ;

HURSTHOUSE, MB .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (09) :1959-1961

[4] THE PREPARATION AND STRUCTURE OF SOME DERIVATIVES OF 3-HYDROXYPYRROLE [J].

DAVOLL, J .

JOURNAL OF THE CHEMICAL SOCIETY, 1953, (DEC) :3802-3811

[5] THERMAL FUNCTIONALIZATION OF NITROGEN SUBSTITUENTS - FORMATION OF DIHYDROPYRROL-3-ONES, QUINOLIN-4-ONES, AND ENAMINOENAMINONES BY GAS-PHASE HYDROGEN TRANSFER-REACTIONS [J].

GORDON, HJ ;

MARTIN, JC ;

MCNAB, H .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (17) :957-958

[6]

LI H, 1996, IN PRESS HETEROCYCLE

[7] DIETHYL 2,4-DIOXOIMIDAZOLIDINE-5-PHOSPHONATES - HORNER-WADSWORTH-EMMONS REAGENTS FOR THE MILD AND EFFICIENT PREPARATION OF C-5 UNSATURATED HYDANTOIN DERIVATIVES [J].

MEANWELL, NA ;

ROTH, HR ;

SMITH, ECR ;

WEDDING, DL ;

WRIGHT, JJK .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (24) :6897-6904

[8]

SCHARF H, 1994, ANGEW CHEM INT EDIT, V33, P2009

[9]

Wasserman H.H., 1981, TETRAHEDRON S, V9S, P191

[10] SINGLET OXYGEN OXIDATION OF BIPYRROLES - TOTAL SYNTHESIS OF D,L-ISOCHRYSOHERMIDIN AND MESO-ISOCHRYSOHERMIDIN [J].

WASSERMAN, HH ;

DESIMONE, RW ;

BOGER, DL ;

BALDINO, CM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (18) :8457-8458

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