Stereoselective synthesis of new selenium-containing heterocycles by cyclocarbonylation of aminoalkynes with carbon monoxide and selenium

被引:31
作者
Fujiwara, S [1 ]
Shikano, Y
Shin-Ike, T
Kambe, N
Sonoda, N
机构
[1] Osaka Dent Univ, Dept Chem, Hirakata, Osaka 5731121, Japan
[2] Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
[3] Kansai Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5648680, Japan
关键词
D O I
10.1021/jo025707d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of 3-aminoalkynes 2 with carbon monoxide and selenium yielded 5-alkylideneselenazolin-2-ones 3 stereoselectively via cycloaddition of in situ generated carbamoselenoates to the carbon-carbon triple bond. 4-Aminoalkyne 7 also afforded the corresponding six-membered selenium-containing heterocycle with the aid of CuI.
引用
收藏
页码:6275 / 6278
页数:4
相关论文
共 46 条
[1]  
[Anonymous], SELENIUM BIOL MED
[2]  
[Anonymous], TOPICS CURRENT CHEM
[3]  
ARYA VP, 1977, INDIAN J CHEM B, V15, P133
[4]  
Back T. G., 1999, ORGANOSELENIUM CHEM
[5]  
BADISCHE ANILIN SODA, Patent No. 1164411
[6]   Novel cleavage of propargylamines by reaction with organolithium compounds [J].
Barluenga, J ;
Canteli, RM ;
Florez, J .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) :3646-3649
[7]   N-SUBSTITUTED LITHIUM 2-LITHIOALLYLAMINES - NEW INTERMEDIATES IN SYNTHESIS [J].
BARLUENGA, J ;
FOUBELO, F ;
FANANAS, FJ ;
YUS, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (03) :553-557
[8]   PROTOTROPIC REARRANGEMENT OF SECONDARY PROPARGYLIC AMINES [J].
BENEFRAIM, DA .
TETRAHEDRON, 1973, 29 (24) :4111-4125
[9]   TIN RADICAL-ADDITION TO ALKYNYL SULFIDES - REACTIVITY OF THE INTERMEDIATE THIOALKYL-SUBSTITUTED BETA-(TRIBUTYLSTANNYL)VINYL RADICALS [J].
CAPELLA, L ;
MONTEVECCHI, PC ;
NANNI, D .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) :3368-3374
[10]   Vinylic selenides and tellurides - Preparation, reactivity and synthetic applications [J].
Comasseto, JV ;
Ling, LW ;
Petragnani, N ;
Stefani, HA .
SYNTHESIS-STUTTGART, 1997, (04) :373-&