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

1
Department of Chemical Technology of Drugs, Medical University of Gdańsk, 107 Gen. J. Hallera Str., 80-416 Gdańsk, Poland
2
Faculty of Chemistry, A. Mickiewicz University, 60-780 Poznań, Poland
*
Author to whom correspondence should be addressed.
Molecules 2004, 9(3), 86-101; https://doi.org/10.3390/90300086
Received: 21 January 2004 / Accepted: 6 February 2004 / Published: 28 February 2004
(This article belongs to the Special Issue Biologically Relevant Heterocyclic Compounds)
Synthesis of novel 5-methylidene-1,2,3,5-tetrahydro[2,1-b]-quinazolinederivatives 2-4 with potential biological activities mediated by α-adrenergic and/orimidazoline receptors was performed by reacting 2-chloro-4,5-dihydroimidazole (1) withthe corresponding 2-aminoacetophenones. Compound 2, which incorporates an enaminemoiety, underwent a 1,3-dipolar cycloaddition reaction with the appropriate nitrones 5-9to 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 furthertreated with acetyl chloride, benzoyl chloride and mesyl chloride to give the 1-substitutedderivatives 17, 18 and 19, respectively. The structures of all new compounds obtainedwere confirmed by elemental analysis and spectral data (IR, 1H- and 13C-NMR) as well asX-ray crystallographic analysis of 3 and 18. View Full-Text
Keywords: 5-Methylidene-1; 2; 3; 5-tetrahydroimidazo[2; 1-b]quinazolines; 1; 3-dipolar cycloaddition; alkylation; acylation; X-ray structure analysis. 5-Methylidene-1; 2; 3; 5-tetrahydroimidazo[2; 1-b]quinazolines; 1; 3-dipolar cycloaddition; alkylation; acylation; X-ray structure analysis.
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Kornicka, A.; Sączewski, F.; Gdaniec, M. Synthesis, Molecular Structure and Reactivity of 5-Methylidene-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolines. Molecules 2004, 9, 86-101.

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