Ring-opening cyclization of alkylidenecyclopropyl ketones with amines. An efficient synthesis of 2,3,4-trisubstituted pyrroles

被引：94

作者：

Lu, LH

Chen, GF

Ma, SM

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China

[2] Zhejiang Univ, Dept Chem, Lab Mol Recognit & Synth, Hangzhou 310027, Peoples R China

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 05期

关键词：

D O I：

10.1021/ol052797a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient synthesis of 2,3,4-trisubstituted pyrroles via intermolecular cyclization of alkylidenecyclopropyl ketones with amines was observed. The addition of anhydrous MgSO4 improved the yields of the products 3. A possible mechanism involving the distal cleavage of the C-C bond of cyclopropane ring was proposed.

引用

收藏

页码：835 / 838

页数：4

相关论文

共 56 条

[1]

Agami C, 2003, SYNTHESIS-STUTTGART, P859

[2] A combinatorial scaffold approach based upon a multicomponent reaction [J].

Bertozzi, F ;

Gundersen, BV ;

Gustafsson, M ;

Olsson, R .

ORGANIC LETTERS, 2003, 5 (09) :1551-1554

[3] Synthesis of mono-, di-, and trisilyl-substituted alkenes via the hydrosilylation of methylenecyclopropanes catalyzed by Rh(I) complexes [J].

Bessmertnykh, AG ;

Blinov, KA ;

Grishin, YK ;

Donskaya, NA ;

Tveritinova, EV ;

Yureva, NM ;

Beletskaya, IP .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (17) :6069-6076

[4] Catalytic multicomponent synthesis of highly substituted pyrroles utilizing a one-pot Sila-Stetter/Paal-Knorr strategy [J].

Bharadwaj, AR ;

Scheidt, KA .

ORGANIC LETTERS, 2004, 6 (14) :2465-2468

[5]

BINGER P, 1987, TOP CURR CHEM, V135, P77

[6] REARRANGEMENT OF ISOXAZOLINE-5-SPIRO DERIVATIVES .8. SELECTIVE FORMATION OF TETRAHYDROPYRIDONES FROM C,C-DISUBSTITUTED NITRONES [J].

BRANDI, A ;

DURUST, Y ;

CORDERO, FM ;

DESARLO, F .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (21) :5666-5670

[7] Synthesis of methylene- and alkylidenecyclopropane derivatives [J].

Brandi, A ;

Goti, A .

CHEMICAL REVIEWS, 1998, 98 (02) :589-635

[8] Heterocycles from alkylidenecyclopropanes [J].

Brandi, A ;

Cicchi, S ;

Cordero, FM ;

Goti, A .

CHEMICAL REVIEWS, 2003, 103 (04) :1213-1269

[9] Palladium-catalyzed addition of alcohol pronucleophiles to alkylidenecyclopropanes [J].

Camacho, DH ;

Nakamura, I ;

Saito, S ;

Yamamoto, Y .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (01) :270-275

[10] SYNTHESIS OF ALPHA-AMINO-METHYLENECYCLOPROPANEPROPIONIC ACID (HYPOGLYCIN-A) [J].

CARBON, JA ;

MARTIN, WB ;

SWETT, LR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (04) :1002-1002

← 1 2 3 4 5 6 →