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Paper | Regular issue | Vol 96, No. 3, 2018, pp.425-439
Published online, 20th February, 2018
DOI: 10.3987/COM-17-13862
■ Novel One-Pot Synthesis of Dihydroacenaphtho[1,2-f][1,3]oxazepines via 1,4-Dipolar Cycloaddition Reaction

Mervat S. Sammor, Mustafa M. El-Abadelah,* Ahmad Q. Hussein, and Firas F. Awwadi

*Department of Chemistry, Faculty of Science, The University of Jordan, Amman 11942, Jordan

Abstract

A facile three-component reaction involving 3-alkyl(aryl)imidazo[1,5-a]pyridines 7a-g, dimethyl acetylenedicarboxylate 2 (DMAD) and acenaphthene-1,2-dione 5 led to the construction of the respective dihydroacenaphtho[1,2-f][1,3]oxazepinedicarboxylates 10a-g in fair yields. Structures of the latter tetracyclic adducts, are based on NMR and MS spectral data and confirmed by single-crystal X-ray diffraction analysis for compound 10a. Most logically, the reaction proceeds via initial formation of the relevant diastereomeric spiro[1,3]oxazine-1,4-dipolar cycloadducts 12, 13 which then suffer skeletal rearrangement leading to the respective acenaphtho[1,2-f]-[1,3]oxazepines 10a-g.