Reaction of 2-formyl imidazole with intermediates from the Baylis-Hillman reaction

被引：24

作者：

Drewes, SE ^{[1
]}

Horn, MM ^{[1
]}

Ramesar, N ^{[1
]}

机构：

[1] Univ Natal, Dept Chem & Chem Technol, ZA-3209 Pietermaritzburg, South Africa

来源：

SYNTHETIC COMMUNICATIONS | 2000年 / 30卷 / 06期

关键词：

D O I：

10.1080/00397910008087122

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of formyl imidazole (in the presence and absence of DABCO, and with either THF or methanol as solvent) with alpha-hydroxylaryl derivatives of methyl acrylate affords novel synthetic intermediates. By controlling the reaction conditions, either allylic substitution products (THF, DABCO) or rearrangement (MeOH, no DABCO) products result.

引用

页码：1045 / 1055

页数：11

共 18 条

[1] RATE ENHANCEMENT EFFECTS IN THE DABCO CATALYZED SYNTHESIS OF HYDROXYALKENOATE ESTERS
AMEER, F
DREWES, SE
FREESE, S
KAYE, PT
[J]. SYNTHETIC COMMUNICATIONS, 1988, 18 (05) : 495 - 500
[2] NECIC ACID SYNTHONS .2. REGIOSELECTIVITY IN THE REACTIONS OF (Z)-2-BROMOMETHYL-2-ALKENOATE ESTERS WITH SELECTED CARBON NUCLEOPHILES
AMEER, F
DREWES, SE
EMSLIE, ND
KAYE, PT
MANN, RL
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (10): : 2293 - 2295
[3] [Anonymous], COMMUNICATION
[4] The Baylis-Hillman reaction: A novel carbon-carbon bond forming reaction
Basavaiah, D
Rao, PD
Hyma, RS
[J]. TETRAHEDRON, 1996, 52 (24) : 8001 - 8062
[5] BERTHE MC, 1994, Patent No. 5332836
[6] INDOLIZINE STUDIES .2. SYNTHESIS AND NMR SPECTROSCOPIC ANALYSIS OF 2-SUBSTITUTED INDOLIZINES
BODE, ML
KAYE, PT
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (15): : 1809 - 1813
[7] A NEW SYNTHESIS OF INDOLIZINES VIA THERMAL CYCLIZATION OF 2-PYRIDYL DERIVATIVES
BODE, ML
KAYE, PT
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (09): : 2612 - 2613
[8] Ciganek E., 1997, ORG REACTIONS, V51, P201
[9] SYNTHETIC POTENTIAL OF THE TERTIARY-AMINE-CATALYSED REACTION OF ACTIVATED VINYL CARBANIONS WITH ALDEHYDES
DREWES, SE
ROOS, GHP
[J]. TETRAHEDRON, 1988, 44 (15) : 4653 - 4670
[10] CHIRAL, CYCLIC AMINO ALDEHYDES IN THE BAYLIS-HILLMAN REACTION - A ROUTE TO SPHINGOSINE ANALOGS
DREWES, SE
KHAN, AA
ROWLAND, K
[J]. SYNTHETIC COMMUNICATIONS, 1993, 23 (02) : 183 - 188

← 1 2 →