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Synthesis 1990; 1990(8): 713-717
DOI: 10.1055/s-1990-26991
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Eine einstufige Synthese von Azolo-anellierten Derivaten des Pyrido[2,3-d]pyrimidins

Oleg N. Chupakhin* , Vladimir L. Rusinov, Tatjana, L. Pilicheva, Andrej A. Tumashov
  • *Uraler Polytechnisches Institut, 620002, Sverdlovsk, USSR
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Publication Date:
17 September 2002 (online)

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A One-Pot Synthesis of Azolo-annulated Derivatives of Pyrido[2,3-d]pyrimidine 6-Nitro[1,2,4]triazolo- and 6-nitropyrazolo[1,5-a]pyrimidines 1a-h react with malononitrile and ethyl cyanoacetate to yield 9-imino-, 2a-h, and 9-oxo-7-nitro-4,9-dihydroazolo[1,5-a]pyrido-[2,3-d]pyrimidines 4a-g, respectively. By using the N*C*-double-labelled ethyl cyanoacetate in this reaction, its participation as a 1,3-bifunctional reagent was established. Malononitrile or ethyl cyanoacetate provide the C-C-N fragment for the pyridine ring. The mechanism is discussed.