Novel tandem multi-component reactions in the stereoselective synthesis of highly functionalised pyrrolidines

被引：19

作者：

Devi, Natarajan Savitha ^{[1
]}

Perumal, Subbu ^{[1
]}

机构：

[1] Madurai Kamaraj Univ, Sch Chem, Madurai 625021, Tamil Nadu, India

来源：

TETRAHEDRON | 2006年 / 62卷 / 25期

关键词：

pyrrolidine; ethyl; 4-chloroacetoacetate; tandem; Mannich; aldol; X-ray; aldehyde;

D O I：

10.1016/j.tet.2006.04.012

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The four-component reaction of ethyl 4-chloroacetoacetate with aromatic aldehydes and ammonium acetate in a 1:2:1 molar ratio provided a simple and rapid access to highly functionalised pyrrolidines, ethyl 1-acetyl-4-hydroxy-5-[hydroxy(aryl)methyl]-2-aryl-2,3dihydro- 1H-pyrrole-3-carboxylates stereoselectively. This transformation presumably occurs via a tandem Mannich-substitution-acetylationaldol sequence of reactions. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：5931 / 5936

页数：6

共 29 条

[1] PRODILIDINE HYDROCHLORIDE - NEW MODERATELY POTENT ANALGESIC [J].

BATTERMAN, RC ;

KAUFMAN, JE ;

MOURATOFF, GJ .

AMERICAN JOURNAL OF THE MEDICAL SCIENCES, 1964, 247 (01) :62-&

[2] ANALGESIC EFFECT OF PRODILIDINE HYDROCHLORIDE (5054) IN ELDERLY PATIENTS WITH CHRONIC PAIN SYNDROME [J].

BOYLE, RW ;

WIGHTMAN, BK ;

TABET, RC .

JOURNAL OF THE AMERICAN GERIATRICS SOCIETY, 1964, 12 (04) :379-&

[3] Diastereocontrolled synthesis of pyrrolidines by nickel promoted tandem cyclization-quenching of aminobromodienes [J].

Cancho, Y ;

Martín, JM ;

Martínez, M ;

Llebaria, A ;

Moretó, JM ;

Delgado, A .

TETRAHEDRON, 1998, 54 (07) :1221-1232

[4]

Craig DC, 1997, SYNLETT, P1441

[5]

ENRAFNONIUS, 1994, CAD 4 EXPRESS VERSIO

[6] Catalytic, three-component assembly reaction for the synthesis of pyrrolidines [J].

Galliford, CV ;

Beenen, MA ;

Nguyen, ST ;

Scheidt, KA .

ORGANIC LETTERS, 2003, 5 (19) :3487-3490

[7] Novel tandem reactions of 2,2′-sulfonylbis(1,3-diarylprop-2-en-1-ones) with hydrazine:: formation of 3,6-diarylpyridazines and 3,5-diarylpyrazoles [J].

Gnanadeepam, M ;

Selvaraj, S ;

Perumal, S ;

Renuga, S .

TETRAHEDRON, 2002, 58 (11) :2227-2230

[8]

HARMS K, 1995, XCAD4

[9]

Hartel W, 1966, Med Klin, V61, P552

[10]

HITOMI M, 1972, ARZNEI-FORSCHUNG, V22, P953

← 1 2 3 →