A novel and facile synthesis of dienals and substituted 2H-pyrans via the Vilsmeier reaction of α-oxo-ketenedithioacetals

被引:34
作者
Liu, YC [1 ]
Dong, DW [1 ]
Liu, Q [1 ]
Qi, YM [1 ]
Wang, Z [1 ]
机构
[1] NE Normal Univ, Dept Chem, Changchun 130024, Peoples R China
关键词
D O I
10.1039/b313977h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel and facile synthesis of dienals (3a, 3b) and substituted 2H-pyrans (4c, 4d) from a series of alpha-oxo ketene-dithioacetals containing a methyl group adjacent to the carbonyl group (1a - d) via the Vilsmeier reaction has been developed and a mechanism for the reactions has been proposed.
引用
收藏
页码:28 / 30
页数:3
相关论文
共 28 条
[1]   SYNTHETISCHE REAKTIONEN VON DIMETHYLFORMAMID .4. DARSTELLUNG VON BETA-CHLORVINYLALDEHYDEN AUS CARBONYLVERBINDUNGEN [J].
ARNOLD, Z ;
ZEMLICKA, J .
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1959, 24 (07) :2385-2392
[2]  
ARNOLD Z, 1958, P CHEM SOC LONDON, P227
[3]   A facile access to 2-methylthio/alkoxy/amino-3-acylimidazo[1,2-a]pyridines based on cupric chloride promoted oxidative ring closure of α-oxoketene N,S-, N,O-, and N,N-acetals [J].
Barun, HO ;
Ila, H ;
Junjappa, H ;
Singh, OM .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (05) :1583-1587
[4]  
BURN D, 1973, CHEM IND-LONDON, P870
[5]   ALPHA-OXO KETENE DITHIOACETALS AND RELATED-COMPOUNDS - VERSATILE 3-CARBON SYNTHONS [J].
DIETER, RK .
TETRAHEDRON, 1986, 42 (12) :3029-3096
[6]  
Dong DW, 1997, CHEM J CHINESE U, V18, P68
[7]   A synthetic approach to the pseudopterosins [J].
Gill, S ;
Kocienski, P ;
Kohler, A ;
Pontiroli, A ;
Qun, L .
CHEMICAL COMMUNICATIONS, 1996, (15) :1743-1744
[8]  
IAN C, 1999, TETRAHEDRON LETT, P4069
[9]   ALPHA-OXOKETENE-S,S-ACETAL, N,S-ACETAL AND N,N-ACETAL - VERSATILE INTERMEDIATES IN ORGANIC-SYNTHESIS [J].
JUNJAPPA, H ;
ILA, H ;
ASOKAN, CV .
TETRAHEDRON, 1990, 46 (16) :5423-5506
[10]   Preparation of lithium 5-lithiomethyl-3-methylpyrazole-1-carboxylate and its reaction with α-oxoketene dithioacetals:: A new general method for substituted and annelated pyrazolo[1,5-a] pyridines [J].
Kishore, K ;
Reddy, KR ;
Suresh, JR ;
Ila, H ;
Junjappa, H .
TETRAHEDRON, 1999, 55 (24) :7645-7652