Studies on Substituted Heteroarenes: New Synthesis of Substituted Pyrrole, Pyridine, Pyrazolo[4,3-bpyridine, Pyrano [3,2-c]quinoline, Benzo [f] chromene, Benzo[h] chromene, Chromeno [8,7-h]chromene, Chromeno[6,5-f] chromene and 2H-chromene Derivatives

Abstract

SEVERAL new pyrazolo[4,3- b] pyridines )7a,b( were prepared by reacting arylmethylenenitriles )1a,c or 1i,j( with 4-nitrosoantipyrine )4(. Reacting 1a,b,d with 4-azidomethylcarbonylantipyrine 8 gave 2-aminopyrrole (14). Pyrano[3,2-c] quinolines (20a,b and 23) were obtained by reacting 4-hydroxyquinoline (15) with 1g, h;2b, respectively.Reaction of 1 with naphthalenediols 24,27 and 29 yield naphthodipyrans 26a,b,28a,b and 30a,b, respectively. Spironaphthodipyrans (32,33) and spironaphthopyrans (36,37) were prepared through reaction of 2a with naphthalenediols (24,27,34 and 35), respectively. Condensation of thioxothiazole (38) with 3,5-dibromo-2-hydroxybenzaldehyde gave 2H-chromene-3-carboxamide (42). 38 also reacted with 1c and 2a to gave 3,5-dicyanopyridines (45 and 47), respectively. Reaction of 2-cyano-N`-(1-thiophen-2-yl)ethylidene) acetohydrazide (49) with 1a,b afforded 3,5-dicyanopyridines (53).

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History

  • Receive Date: 24 November 2011
  • Revise Date: 18 September 2012
  • Accept Date: 19 September 2012

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