The chemical behavior of 4,9-dimethoxy-5-oxo-5H-furo[3,2-g]chromene-6-carbonitrile (khellin-6-carbonitrile) (1) was examined towards a variety of nitrogen nucleophiles. Some novel Schiff bases 5-7 were prepared from reaction of carbonitrile 1 with some heterocyclic amines. Treatment of carbonitrile 1 with some hydrazine derivatives in boiling ethanol afforded pyrazole derivatives 8-13. Khellin-6-carbonitrile (1) reacted with hydrazine hydrate and phenylhydrazine in acetic acid to afford angular heteroannulated furo[3`,2`:6,7]chromeno[4,3-c]pyrazol-4(1H)-one derivatives 14 and 15. Triazolo[1,5-a]pyrimidine 16 and pyrimido[1,2-a]benzimidazole 17 were synthesized through ring opening and recyclization reactions of compound 1 with 3-amino-1,2,4-triazole and 2-aminobenzimidazole, respectively. Reaction of compound 1 with guanidine and cyanoguanidine in ethanolic potassium hydroxide solution resulted in ring conversion giving the novel angular furo[3`,2`:6,7]chromeno[4,3-d]pyrimidin-5-ones 18 and 19. The antimicrobial activity of the prepared compounds appeared distinguish activity against the selected microorganisms.

中文翻译：

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4,9-二甲氧基-5-氧代-5的反应性

检查了4,9-二甲氧基-5-氧代-5 H-呋喃[3,2 - g ]色烯-6-腈（khellin-6-腈）（1 ）对各种氮亲核试剂的化学行为。一些新颖的席夫碱5 - 7从腈反应制备1与某些杂环胺。腈的治疗1在沸腾的乙醇，得到的吡唑衍生物的一些肼衍生物8 - 13 。Khellin-6-腈（1 ）与水合肼和苯肼在乙酸中反应，得到角杂芳基呋喃[3`，2`：6,7] chromeno [4,3 - c ] pyrazol -4（1）H ）-一阶导数14和15 。通过化合物1分别与3-氨基-1,2,4-三唑和2-氨基苯并咪唑的开环和再循环反应，合成了三唑并[1,5- a ]嘧啶16和嘧啶基[1,2- a ]苯并咪唑17 。在乙醇氢氧化钾溶液中化合物1与胍和氰基胍的反应导致环转化，得到新颖的角型呋喃[3`，2`：6,7] chromeno [4,3 - d ]嘧啶-5-酮18和19。制备的化合物的抗微生物活性似乎对选定的微生物具有区别活性。