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.
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(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
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