Synthesis of Oxazines and Dioxanes from Aziridines and Epoxides

S. Bhadra; L. Adak; S. Samanta; A. K. M. M. Islam; M. Mukherjee; B. C. Ranu

doi:10.1055/s-0030-1259463

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Synfacts 2011(3): 0339-0339
DOI: 10.1055/s-0030-1259463

Polymer-Supported Synthesis

Synthesis of Oxazines and Dioxanes from Aziridines and Epoxides

Contributor(s): Yasuhiro Uozumi, Tsubasa Muto
S. Bhadra, L. Adak, S. Samanta, A. K. M. M. Islam, M. Mukherjee, B. C. Ranu*
Indian Association for the Cultivation of Science, Kolkata and Saha Institute of Nuclear Physics, Kolkata, India

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Publication History

Publication Date:
16 February 2011 (online)

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Significance

Alumina-supported copper(II) (Cu/Al₂O₃) catalyzed the regioselective ring opening of aziridines 2 and epoxides 4 and the subsequent cyclization with ortho-iodo phenols 1 to give the corresponding 1,4-benzoxadines 3 in up to 98% yield (18 examples) and 1,4-benzodioxanes 5 in up to 81% yield (9 examples), respectively.