153258-60-7Relevant academic research and scientific papers
CHEMISTRY AND CYCLIZATION REACTIONS OF THIENOQUINOXALINE DERIVATIVES: PART I
Badr, M. Z. A.,Mahgoub, S. A.,Moustafa, O. S.,Geies, A. A.
, p. 77 - 86 (2007/10/02)
Reaction of 2(1H)-quinoxalinethione-3-carbonitrile 1 with alkyl or aralkyl halides, chloroacetic acid, ethyl chloroacetate, or N-phenylchloroacetamide in ethanolic sodium acetate solution gives the corresponding 3-thioethers of 1.Traetment of 3 with acetic anhydride gives the dimesoionic thiazolo-2-cyanoquinoxaline, 4. Treatment of 6 or 10 with ethanolic sodium ethoxide solution gives the cyclization products, ethyl 3-aminothienoquinoxaline-2-carboxylate 7 or 3-phenylcarboxamide 11 substituents respectively.Treatment of 11 with carbon disulfide/ethanolic potassium hydroxide solution gives 3-phenylpyrimidothienoquinoxaline-4-one-2-thione 12 which is also produced by treatment of 7 with phenyl isothiocyanate in dry pyridine.Compound 11 cyclizes on treatment with benzoyl chloride, acetic anhydride, phenyl isothiocyanate, ethyl chloroformate and/or nitrous acid, to produce the corresponding pyrimidothienoquinoxalines 14-17 and triazinothienoquinoxaline 18 derivatives respectively.Compound 7 cyclizes with ethanolic potassium hydroxide solution followed by acetic anhydride to give the oxazino compound 19 which gives (with different amino reagents) the corresponding 3-substituted pyrimidothienoquinoxaline-4-ones 20-25. Key words: Thienoquinoxaline; pyrimidothienoquinoxaline; synthesis and reacctions; antimicrobial activities.
