7-데아자퓨린 유도체의 합성

Synthesis of 7-Deazapurine Derivatives

A new series of 7-deazapurine derivatives[7,8] as purine antagonists was prepared. Diethyl 4-cyano-N-(diphenylmethylene)-3-arylglutamate[3] were synthesized by LDA-catalyzed Michael addition of N-(diphenylmethylene)glycine ethyl ester with (E)-2-cyano-3-arylacrylate. Deprotection yields diethyl 4-cyano-3-arylglutamate, which were easily cyclized to 4-cyano-2-ethoxycarbonyl-5-oxo-3-arylpyrrolidine[4]. The compounds[4] were treated with NaBH4 and then with (C2H5)3OBF4 to give 4-cyano-5-ethoxy-2H-2-ethoxymethyl-3-aryl-3,4-dihydropyrrole[6], which were converted to 7-aryl-6-amino-8-ethoxymethyl-7,8-dihydro-7(3H, 9H)-deazapurine-2-thione[7] and 7-aryl-2,6-diamino-8-ethoxymethyl-7,8-dihydro-7(9H)-deazapurine[8] with possible activity against neoplastic disease.