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Paper | Regular issue | Vol 63, No. 4, 2004, pp.797-807
Published online, 6th February, 2004
DOI: 10.3987/COM-03-9973
■ An Interaction of 2-Thiazoleacetonitriles with N-(2-Chloroacetyl)anthranilic Acid Ester

Elizaveta V. Resnyanska, Anton V. Tverdokhlebov,* Andrey A. Tolmachev, Yulian M. Volovenko, and Tatyana V. Shokol

*'Enamine Ltd.' Co., I. Kudri str. 31, apt. 17, 02042, Kiev, Ukranie

Abstract

The title ester was found to react with 2-benzothiazoleacetonitrile yielding 3-(2-benzothiazolyl)-2,4-dihydropyrrolo[1,2-a]quinazoline-1,5-dione. At the same time 4-aryl-2-thiazoleacetonitriles gave 3,4-dihydro-β,4-dioxo- α,δ-bis(4-aryl-2-thiazolyl)-2-quinazolinepentanenitriles potassium salts under identical conditions. These results were explained in terms of different solubility of the intermediate compounds. Upon acidification the obtained salts were shown to undergo intramolecular Thorpe addition leading to the 3-amino-2,4-bis(4-aryl-2-thiazolyl)-4-[4(3H)-oxo-2-quinazolinyl]-2-cyclopenten-1-ones. Above mentioned pyrrolo[1,2-a]quinazoline derivative was treated with benzylamines and active methylene nitriles to yield β-(2-benzothiazolyl)-N-arylmethyl-3,4-dihydro-4-oxo-2-quinazolinepropanamides and 2-substituted 3-amino-4-(2-benzothiazolyl)-4-[4(3H)-oxo-2-quinazolinyl]-2-cyclopenten-1-ones, respectively.