Tetrahedron

Solid phase synthesis of 6-acylamino-1-alkyl/aryl-4-oxo-1, 4-dihydrocinnoline-3-carboxamides

L Sereni, M Tató, F Sola, WKD Brill

Index: Sereni, Laura; Tato, Marco; Sola, Francesco; Brill, Wolfgang K.-D. Tetrahedron, 2004 , vol. 60, # 38 p. 8561 - 8577

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Citation Number: 8

Abstract

6-Acylmino-1-alkyl/aryl-4-oxo-1, 4-dihydrocinnoline-3-carboxamides were synthesized in parallel from 6-nitro-4-oxo-1, 4-dihydrocinnoline-3-carboxylic acid. The latter formed amides with amines bound to polystyrene-based resins via acid-labile linkers. N1 and N2-alkylation, followed by alkyl migration yielded only N1-alkylated products. Reduction of the 6-nitro group and acylation concluded the synthesis.