Phosphine-catalyzed construction of sulfur heterocycles

被引：81

作者：

Gabillet, Sandra ^{[1
]}

Lecercle, Delphine ^{[1
]}

Loreau, Olivier ^{[1
]}

Carboni, Michael ^{[1
]}

Dezard, Sophie ^{[1
]}

Gomis, Jean-Marie ^{[1
]}

Taran, Frederic ^{[1
]}

机构：

[1] CEA, iBiTecS, Serv Chim Bioorgan & Marquage, F-91191 Gif Sur Yvette, France

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 20期

关键词：

ONE-POT SYNTHESIS; MICROWAVE IRRADIATION; RHODANINE DERIVATIVES; INHIBITORS; 5-ARYLIDENE-2-IMINO-4-THIAZOLIDINONES; ANNULATION; ALKYNES; AGENTS;

D O I：

10.1021/ol701563e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and efficient method for constructing sulfur heterocycles was developed using a phosphine-catalyzed tandem umpolung addition and intramolecular cyclization of bifunctional sulfur pronucleophiles on arylpropiolates. The reaction offers a promising route to synthetically useful as well as biologically active heterocycles under neutral conditions.

引用

页码：3925 / 3927

页数：3

共 35 条

[1] Synthesis and biological evaluation of rhodanine derivatives as PRL-3 inhibitors [J].

Ahn, JH ;

Kim, SJ ;

Park, WS ;

Cho, SY ;

Ha, JD ;

Kim, SS ;

Kang, SK ;

Jeong, DG ;

Jung, SK ;

Lee, SH ;

Kim, HM ;

Park, SK ;

Lee, KH ;

Lee, CW ;

Ryu, SE ;

Choi, JK .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (11) :2996-2999

[2]

[Anonymous], COMPREHENSIVE MEDICI

[3] 4-THIAZOLIDINONES [J].

BROWN, FC .

CHEMICAL REVIEWS, 1961, 61 (05) :463-521

[4] Rhodanine derivatives as inhibitors of JS']JSP-1 [J].

Cutshall, NS ;

O'Day, C ;

Prezhdo, M .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (14) :3374-3379

[5] Axially chiral 2-arylimino-3-aryl-thiazolidine-4-one derivatives: Enantiomeric separation and determination of racemization barriers by chiral HPLC [J].

Erol, Sule ;

Dogan, Ilknur .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (07) :2494-2500

[6] Synthesis, activity, and molecular modeling of new 2,4-dioxo-5-(naphthylmethylene)-3-thiazolidineacetic acids and 2-thioxo analogues as potent aldose reductase inhibitors [J].

Fresneau, P ;

Cussac, M ;

Morand, JM ;

Szymonski, B ;

Tranqui, D ;

Leclerc, G .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (24) :4706-4715

[7] Phosphine-catalyzed tandem α-O-addition and transesterification of oxgen pronucleophiles on arylpropiolates:: A new route to dioxygenated heterocyles [J].

Gabillet, Sandra ;

Lecercle, Delphine ;

Loreau, Olivier ;

Dezard, Sophie ;

Gomis, Jean-Marie ;

Taran, Frederic .

SYNTHESIS-STUTTGART, 2007, (04) :515-522

[8] The synthesis and SAR of rhodanines as novel class C β-lactamase inhibitors [J].

Grant, EB ;

Guiadeen, D ;

Baum, EZ ;

Foleno, BD ;

Jin, HY ;

Montenegro, DA ;

Nelson, EA ;

Bush, K ;

Hlasta, DJ .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (19) :2179-2182

[9]

HANEFELD W, 1992, LIEBIGS ANN CHEM, P337

[10] One pot synthesis of thiazolodihydropyrimidinones and evaluation of their anticancer activity [J].

Holla, BS ;

Rao, BS ;

Sarojini, BK ;

Akberali, PM .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2004, 39 (09) :777-783

← 1 2 3 4 →