Functionally Substituted 1,2,4-Triazoloquinoline, Tetrahydro-quinolinone and Benzotriazolotriazine Derivatives from 5,5-Dimethylcyclohexan-1,3-Dione and Arylmethylenemalonic Acid Derived Michael Acceptors

Abstract

 SEVERAL new functionally [1,2,4]triazolo[1,5-a]quinoline-4- …… carbonitriles (8a-c) and [1,2,4] triazolo[1,5-a]quinoline-4-carbox-amides 12a,b were prepared from Nʹ-(5,5-dimethyl-3-oxocyclohexen-1-yl)benzohydrazide (5) and arylmethylene nitriles 2a-c and 2d,e, respactively.Reacting 2-oxo-3H-indol-3-ylidene malonic acid derivatives 3a,b with 5 afforded dioxospiro [3H-indole-3,4ʹ-quinoline]-3ʹ-carbonitrile (15) and 2- oxo-[1H] indol-3-ylcyanoacetate (17), respactively.Treating 5 with the enaminoester 18 gave hexahydro-7,7-dimethyl-2,5-dioxoquinolin-3-yl]benzamide (20). Coupling of 5 with the aryl diazonium salts and heteroaryl diazonium salts gave the hydrazones (21) and tetrahydro-[1,2,4]triazolo[5,1-c] [1,2,4] benzotriazine-6-ylidene)benzohydrazide (26).

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History

  • Receive Date: 05 September 2011
  • Revise Date: 18 September 2012
  • Accept Date: 19 September 2012

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