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The starting substrate 5-chloro-4,9-dimethoxy-7-oxo-7 H -furo[3,2- g ]chromene-6-carbonitrile ( 2 ) was efficiently synthesized from chlorination of the corresponding hydroxy derivative. The presence of adjacent cyano and chloro functions was employed for construction a variety of five, six and seven membered rings annulated furo[3,2- g ]chromenes. Treating precursor  2  with hydrazine, phenylhydrazine and hydroxylamine yielded furo[3,2:6,7]chromeno[4,3- c ]pyrazoles  3 ,  4  and furo[3,2:6,7] chromeno[3,4- d ]isoxazole  5 , respectively. Also, reaction of compound  2  with a diversity of 1,3- N , N -binucleophiles such as guanidine, cyanoguanidine, thiourea, acetamidine and benzamidine produced annulated furo[3,2:6,7]chromeno[4,3- d ]pyrimidines  6 – 10 , respectively. Further, treatment of compound  2  with a variety of 1,4-binucleophiles namely ethylenediamine,  o -phenylenediamine and 2-aminophenol yielded furo[3,2:6,7]chromeno[4,3- e ][1,4]diazepine  11 , furo[3,2:6,7]chromeno[4,3- b ][1,5]benzodiazepine  12  and furo[3,2:6,7]chromeno[4,3- b ][1,5]benzoxazepine  13 , respectively. Some of the synthesized compounds seemed good antimicrobial activity especially compounds  3, 6  and  8 . Using analytical and spectral results, the structures of the prepared compounds were established.

Synthetic strategies, characterization and antimicrobial evaluation of novel angular heteroannulated furo[3,2- g ]chromenes