Synthesis of Novel 4-Aminotetrahydropyrrolo[1,2-a]quinazoline Derivatives

Chemistry of Heterocyclic Compounds 2013
Daina Zicāne, Zenta Tetere, Irisa Rāviņa, Māris Turks

Decarboxylation of substituted monohydrazides of 6-arylcyclohex-3-ene-1,1-dicarboxylic acids proceeds stereospecifically and leads to 1,6-cis-disubstituted cyclohex-3-enes. Due to the presence of anthranilic acid moiety these decarbboxylated hydrazides undergo formation of pyrrolo[1,2-alfa]quinazolines when treated with 2-oxoglutaric acid. The present paper describes the first example of chemoselective synthesis of amide-linked conjugates between cyclohexene moiety and tetrahydropyrrolo[1,2-a]quinazolines.

Keywords
cyclohexene carboxylic acid hydrazides, 2-oxoglutaric acid, pyrrolo[1,2-a]quinazolines, amide linker, stereospecific decarboxylation
DOI
10.1007/s10593-013-1248-7
Hyperlink
http://link.springer.com/article/10.1007%2Fs10593-013-1248-7

Zicāne, D., Tetere, Z., Rāviņa, I., Turks, M. Synthesis of Novel 4-Aminotetrahydropyrrolo[1,2-a]quinazoline Derivatives. Chemistry of Heterocyclic Compounds, 2013, Vol.49, Iss.2, pp.310-316. e-ISSN 1573-8353. ISSN 0009-3122. Available from: doi:10.1007/s10593-013-1248-7

Publication language
English (en)