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Molecules 2004, 9(3), 86-101; doi:10.3390/90300086
Article

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

1, 1,*  and 2
Received: 21 January 2004; Accepted: 6 February 2004 / Published: 28 February 2004
(This article belongs to the Special Issue Biologically Relevant Heterocyclic Compounds)
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Abstract: 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.
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.
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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.

AMA Style

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(3):86-101.

Chicago/Turabian Style

Kornicka, Anita; Sączewski, Franciszek; Gdaniec, Maria. 2004. "Synthesis, Molecular Structure and Reactivity of 5-Methylidene-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolines." Molecules 9, no. 3: 86-101.



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