First example of electrophile induced Baylis-Hillman reaction: a novel facile one-pot synthesis of indolizine derivatives

被引:71
作者
Basavaiah, D [1 ]
Rao, AJ [1 ]
机构
[1] Univ Hyderabad, Sch Chem, Hyderabad 500046, Andhra Pradesh, India
关键词
D O I
10.1039/b211349j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Treatment of pyridine-2-carboxaldehyde with activated alkenes such as alkyl vinyl ketones and cyclic enones in the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) provides a novel facile one-pot synthesis of indolizine derivatives, thus for the first time describing an electrophile induced Baylis-Hillman reaction.
引用
收藏
页码:604 / 605
页数:2
相关论文
共 25 条
[1]   The use of enantiomerically pure N-sulfinimines in asymmetric Baylis-Hillman reactions [J].
Aggarwal, VK ;
Castro, AMM ;
Mereu, A ;
Adams, H .
TETRAHEDRON LETTERS, 2002, 43 (08) :1577-1581
[2]   Asymmetric Baylis-Hillman reactions: catalysis using a chiral pyrrolizidine base [J].
Barrett, AGM ;
Cook, AS ;
Kamimura, A .
CHEMICAL COMMUNICATIONS, 1998, (22) :2533-2534
[3]   The Baylis-Hillman reaction: A novel carbon-carbon bond forming reaction [J].
Basavaiah, D ;
Rao, PD ;
Hyma, RS .
TETRAHEDRON, 1996, 52 (24) :8001-8062
[4]   The Baylis-Hillman reaction: One-pot facile synthesis of 2,4-functionalized 1,4-pentadienes [J].
Basavaiah, D ;
Sharada, DS ;
Kumaragurubaran, N ;
Reddy, RM .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (20) :7135-7137
[5]   A SIMPLE SYNTHESIS OF ALPHA-METHYLENE-BETA-HYDROXYALKANONES [J].
BASAVAIAH, D ;
GOWRISWARI, VVL .
TETRAHEDRON LETTERS, 1986, 27 (18) :2031-2032
[6]   INDOLIZINE STUDIES .2. SYNTHESIS AND NMR SPECTROSCOPIC ANALYSIS OF 2-SUBSTITUTED INDOLIZINES [J].
BODE, ML ;
KAYE, PT .
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 [J].
BODE, ML ;
KAYE, PT .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (09) :2612-2613
[8]  
Ciganek E., 1997, ORG REACTIONS, V51, P201
[9]   Synthesis of 1,3-disubstituted naphthalenes from the Baylis-Hillman acetates with the aid of manganese(III) acetate [J].
Im, YJ ;
Lee, KY ;
Kim, TH ;
Kim, JN .
TETRAHEDRON LETTERS, 2002, 43 (26) :4675-4678
[10]   The chalcogeno-Baylis-Hillman reaction of ketones and α-dicarbonyl compounds [J].
Kataoka, T ;
Kinoshita, H ;
Kinoshita, S ;
Iwamura, T .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (18) :2043-2045