A novel one-pot synthesis of 3-carbomethoxy-4-arylfuran-2-(5H)-ones from ketones using [hydroxy(tosyloxy)iodo]benzene

被引：22

作者：

Karade, Nandkishor N. ^{[1
]}

Gampawar, Sumeet V. ^{[1
]}

Kondre, Jeevan M. ^{[1
]}

Shinde, Sandeep V. ^{[1
]}

机构：

[1] Swami Ramanand Teerth Marathwada Univ, Sch Chem Sci, Nanded 431606, Maharashtra, India

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 28期

关键词：

hypervalent iodine; gamma-lactone; potassium monomethyl malonate; enolisable ketone;

D O I：

10.1016/j.tetlet.2008.05.012

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel one-pot procedure for the synthesis of 3-carbomethoxy-4-aryl furan-2-(5H)-ones is reported via alpha-tosyloxylation of enolisable ketones with [hydroxy(tosyloxy)iodo]benzene, followed by treatment with potassium monomethyl malonate and K2CO3. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：4402 / 4404

页数：3

共 56 条

[21] Synthesis of bicyclic γ-lactones promoted by Mn(OAc)3:: Regio- and diastereoselectivities
Lamarque, L
Méou, A
Brun, P
[J]. TETRAHEDRON, 1998, 54 (23) : 6497 - 6506
[22] Gold-catalyzed highly efficient access to 3(2H)-furanones from 2-oxo-3-butynoates and related compounds
Liu, Yuanhong
Liu, Meina
Guo, Shenghai
Tu, Huamin
Zhou, Yebing
Gao, Hongjun
[J]. ORGANIC LETTERS, 2006, 8 (16) : 3445 - 3448
[23] Synthesis of chlorinated β- and γ-lactones from unsaturated acids with sodium hypochlorite and Lewis acids
Lopez-Lopez, Jose A.
Guerra, Francisco M.
Moreno-Dorado, F. Javier
Jorge, Zacarias D.
Massanet, Guillermo M.
[J]. TETRAHEDRON LETTERS, 2007, 48 (10) : 1749 - 1752
[24] CuX2-mediated cyclization reaction of 2,3-allenoic acids.: An efficient route to β-halobutenolides
Ma, SM
Wu, SL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (25) : 9314 - 9317
[25] Pd(0)/Ag+-cocatalyzed cyclization reaction of 1,2-allenic carboxylic acids with aryl/alkenyl halides.: An efficient synthesis of butenolides
Ma, SM
Shi, ZJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (18) : 6387 - 6389
[26] CHIRAL BICYCLES FROM RIBONOLACTONE
MANN, J
THOMAS, A
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (11) : 737 - 738
[27] A NOVEL-APPROACH TO CIS-CHRYSANTHEMIC ACIDS
MANN, J
THOMAS, A
[J]. TETRAHEDRON LETTERS, 1986, 27 (30) : 3533 - 3534
[28] Organohypervalent iodine: Development, applications, and future directions
Moriarty, RM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (08) : 2893 - 2903
[29] MORIARTY RM, 1992, SYNTHESIS-STUTTGART, P845
[30] REACTION OF [HYDROXY(TOSYLOXY)IODO]BENZENE AND [HYDROXY(MESYLOXY)IODO]BENZENE WITH TRIMETHYLSILYL ENOL ETHERS - A NEW GENERAL-METHOD FOR ALPHA-SULFONYLOXYLATION OF CARBONYL-COMPOUNDS
MORIARTY, RM
PENMASTA, R
AWASTHI, AK
EPA, WR
PRAKASH, I
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (05) : 1101 - 1104

← 1 2 3 4 5 6 →