Synthesis Molecular Structure Reactivity of 5-Methylidene-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolines

Molecules

Anita Kornicka¹  Franciszek Sၜzewski¹ 

[1] Department of Chemical Technology of Drugs, Medical University of Gdańsk, 107 Gen. J. Hallera Str., 80-416 Gdańsk, Poland

关键词: 5-Methylidene-1;    2;    3;    5-tetrahydroimidazo[2;    1-b]quinazolines;    1;    3-dipolar cycloaddition;    alkylation;    acylation;    X-ray structure analysis;   

DOI  :  10.3390/90300086

来源: mdpi

【 摘 要 】

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^'-diphenylisoxazol-idines 10-14. Reactions of the title compounds 2 and 4 with dimethyl acetylene-dicarboxylate (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.

【 授权许可】

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