title: Azolyacetones as precursors to indoles and naphthofurans facilitated by microwave irradiation with simultaneous cooling.
abstract: Phthalimide reacted with phenacyl bromide under microwave irradiation to yield phenacyl isoindolidene-1,3-dione (3b), while 3a reacted with phenylhydrazine to yield the phenylhydrazone 4 that was readily converted into indoylphthalimide 8. Similarly N-benzotriazolylacetone (6a) reacted with phenyl hydrazine to yield the phenylhydrazone 7a that was converted into indoylbenzotriazole 9. Treatment of 8 with hydrazine hydrate afforded a mixture of phthalhydrazide 10 and 3-amino-2-methylindole (11). Reacting enaminone 13 with naphthoquinone (14) afforded the aryl naphthofuran 17. The possibility of the formation of the aldehyde 18 was excluded based on HMQC, which revealed that the carbonyl carbon is not linked to any hydrogen.
authors.affiliation: Department of Chemistry, Faculty of Science, University of Kuwait, Safat, 13060, P.O. Box 12613, Kuwait. saleh.almousawi@yahoo.com
authors.forename: Saleh Mohammed
authors.initials: SM
authors.lastname: Al-Mousawi
authors.forename: Morsy Ahmed
authors.initials: MA
authors.lastname: El-Apasery
mesh_terms: D000098:Acetophenones / Q000737:chemistry; D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry*; D006835:Hydrazones / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008872:Microwaves; D015394:Molecular Structure; D010797:Phthalimides / Q000737:chemistry
chemical_list: D000098:Acetophenones; D001572:Benzofurans; D006835:Hydrazones; D007211:Indoles; D010797:Phthalimides; C012483:phenylhydrazone; C037431:phthalimide; C013190:phenacyl bromide
references.citation: J Med Chem. 2006 Jun 1;49(11):3332-44
references.pmid: 16722652
references.citation: Bioorg Med Chem. 2007 May 1;15(9):3248-65
references.pmid: 17339113