A novel multicomponent reaction of dimethoxycarbene and DMAD with aldehydes and quinones: facile synthesis of dihydrofuran derivatives

被引:35
作者
Nair, V [1 ]
Bindu, S [1 ]
Balagopal, L [1 ]
机构
[1] CSIR, Reg Res Lab, Div Organ Chem, Trivandrum 695019, Kerala, India
关键词
dimethoxycarbene; acetylenedicarboxylate; aldehydes; quinones; dihydrofuran;
D O I
10.1016/S0040-4039(01)00070-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The zwitterionic species generated by the addition of dimethoxy carbene to dimethyl acetylenedicarboxylate (DMAD) is trapped by aldehydes and quinones to yield dihydrofuran derivatives in good yields. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2043 / 2044
页数:2
相关论文
共 9 条
[1]   CARBENE REACTIONS .4. ADDITION OF DIMETHOXYCARBENE TO C-C MULTIPLE BONDS [J].
HOFFMANN, RW ;
LILIENBL.W ;
DITTRICH, B .
CHEMISCHE BERICHTE-RECUEIL, 1974, 107 (10) :3395-3407
[2]   CARBENE REACTIONS .3. ADDITION OF DIMETHOXYCARBENE TO ISOCYANATES AND ISOTHIOCYANATES [J].
HOFFMANN, RW ;
STEINBAC.K ;
DITTRICH, B .
CHEMISCHE BERICHTE-RECUEIL, 1973, 106 (07) :2174-2184
[3]   CARBENE REACTIONS .7. NUCLEOPHILIC CHARACTER OF DIMETHOXYCARBENE [J].
HOFFMANN, RW ;
REIFFEN, M .
CHEMISCHE BERICHTE-RECUEIL, 1976, 109 (07) :2565-2571
[4]   CARBENE REACTIONS .6. ADDITION OF DIMETHOXYCARBENE TO HETERODIENES [J].
HOFFMANN, RW ;
STEINBACH, K ;
LILIENBLUM, W .
CHEMISCHE BERICHTE-RECUEIL, 1976, 109 (05) :1759-1768
[5]   Novel products from thermolysis of 5,5-dimethyl-2,2-diphenoxy-Δ3-1,3,4-oxadiazoline in the presence of DMAD [J].
Lu, XS ;
Warkentin, J .
ORGANIC LETTERS, 2000, 2 (22) :3501-3503
[6]   The reaction of cyclohexyl isocyanide and dimethyl acetylenedicarboxylate with o- and p-quinones:: a novel synthesis of iminolactones [J].
Nair, V ;
Vinod, AU ;
Nair, JS ;
Sreekanth, AR ;
Rath, NP .
TETRAHEDRON LETTERS, 2000, 41 (34) :6675-6679
[7]   The reaction of cyclohexyl isocyanide and dimethyl acetylenedicarboxylate with aldehydes: a novel synthesis of 2-aminofuran derivatives [J].
Nair, V ;
Vinod, AU .
CHEMICAL COMMUNICATIONS, 2000, (12) :1019-1020
[8]   Silicon migration from oxygen to carbon and decarbonylation in methoxytriphenylsiloxycarbene [J].
Pezacki, JP ;
Loncke, PG ;
Ross, JP ;
Warkentin, J ;
Gadosy, TA .
ORGANIC LETTERS, 2000, 2 (18) :2733-2736
[9]   Δ3-1,3,4-oxadiazolines.: Versatile sources of reactive intermediates [J].
Warkentin, J .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (14) :2161-2169