Molecules p. 86 - 101 (2004)
Update date:2022-07-29
Topics:
Kornicka, Anita
Saczewski, Franciszek
Gdaniec, Maria
Synthesis of novel 5-methylidene-1,2,3,5-tetrahydro[2,1-b]-quinazoline derivatives 2-4 with potential biological activities mediated by α-adrenergic and/or imidazoline receptors was performed by reacting 2-chloro-4,5-dihydroimidazole (1) with the corresponding 2-aminoacetophenones. Compound 2, which incorporates an enamine moiety, underwent a 1,3-dipolar cycloaddition reaction with the appropriate nitrones 5-9 to give 1,2,3,5-tetrahydro-imidazo[2,1-b]quinazolin-5,5′-spiro-2′, 3′-diphenylisoxazolidines 10-14. Reactions of the title compounds 2 and 4 with dimethyl acetylenedicarboxylate (DMAD) afforded dimethyl 2-(2,3-dihydroimidazo[2,1-b]quinazolin-5(1H)-ylidenemethyl)but-2-enedioates 15, 16. Imidazo[2,1-b]quinazoline 2 was further treated with acetyl chloride, benzoyl chloride and mesyl chloride to give the 1-substituted derivatives 17, 18 and 19, respectively. The structures of all new compounds obtained were confirmed by elemental analysis and spectral data (IR, 1H- and 13C-NMR) as well as X-ray crystallographic analysis of 3 and 18.
View MoreJiangxi Dongxu Chemical Science & Technology Co.,Ltd
Contact:+86-791-86899381
Address:Nanchang, Jiangxi, China
website:http://www.orchid-chem.com
Contact:+86-571-85395792
Address:607, North Zhongshan Road, Hangzhou 310000 China
SHIFANG SUHONG CHEMICAL CO.,LTD
Contact:+86-838-2224563
Address:Room 1207 Zongchen Sunshine No.128 Taishan South Road,Deyang City,Sichuan China
Shifang Taifeng New Flame Retardant Co., Ltd
Contact:02884721008
Address:tingjiang industrial park, hefeng town
Contact:+86-717-6370352
Address:168 Chengdong Avenue, Yichang, Hubei 443003, P. R.China
Doi:10.1039/c39810000202
(1981)Doi:10.1021/jo00155a028
(1983)Doi:10.1055/s-1998-1979
(1998)Doi:10.1021/ja044588b
(2005)Doi:10.1139/v82-419
(1982)Doi:10.1007/s10895-017-2078-2
(2017)