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Synthesis of Five-, Six-, and Seven-Membered 1,3- and 1,4-Heterocyclic Compounds via Intramolecular Hydroalkoxylation/Hydrothioalkoxylation of Alkenols/Thioalkenols

Manash J. Deka, Kiran Indukuri, Sabera Sultana, Madhurjya Borah and Anil K. Saikia*

*Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati-781039, India, Email: asaikiaiitg.ernet.in

M. J. Deka, K. Indukuri, S. Sultana, M. Borah, A. K. Saikia, J. Org. Chem., 2015, 80, 4349-4359.

DOI: 10.1021/acs.joc.5b00049 (free Supporting Information)


 

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Abstract

Boron trifluoride etherate mediates an intramolecular hydroalkoxylation/hydrothioalkoxylation of nitrogen-tethered alkenes providing five-membered thiazolidine, six-membered 1,4-oxazines (morpholines) and tetrahydro-2H-1,4-thiazines (thiomorpholines), and seven-membered 1,4-oxazepanes in good yields.


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Key Words

morpholines, thiomorpholines


ID: J42-Y2015