Azolyacetones as precursors to indoles and naphthofurans facilitated by microwave irradiation with simultaneous cooling.
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.
Al-Mousawi
Saleh Mohammed
SM
Department of Chemistry, Faculty of Science, University of Kuwait, Safat, 13060, P.O. Box 12613, Kuwait. saleh.almousawi@yahoo.com
El-Apasery
Morsy Ahmed
MA
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
D000098:Acetophenones; D001572:Benzofurans; D006835:Hydrazones; D007211:Indoles; D010797:Phthalimides; C012483:phenylhydrazone; C037431:phthalimide; C013190:phenacyl bromide
J Med Chem. 2006 Jun 1;49(11):3332-44
16722652
Bioorg Med Chem. 2007 May 1;15(9):3248-65
17339113