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Dang TT, Albrecht U, Gerwien K, et al. One-pot cyclizations of dilithiated oximes and hydrazones with epibromohydrin. Efficient synthesis of 6-hydroxymethyl-5,6-dihydro-4H-1,2-oxazines and oxazolo[3,4-b]pyridazin-7-ones. J Org Chem. 2006;71(6):2293-301doi: 10.1021/jo052329e.
Dang, T. T., Albrecht, U., Gerwien, K., Siebert, M., & Langer, P. (2006). One-pot cyclizations of dilithiated oximes and hydrazones with epibromohydrin. Efficient synthesis of 6-hydroxymethyl-5,6-dihydro-4H-1,2-oxazines and oxazolo[3,4-b]pyridazin-7-ones. The Journal of organic chemistry, 71(6), 2293-301. https://doi.org/10.1021/jo052329e
Dang, Tuan Thanh, et al. "One-pot cyclizations of dilithiated oximes and hydrazones with epibromohydrin. Efficient synthesis of 6-hydroxymethyl-5,6-dihydro-4H-1,2-oxazines and oxazolo[3,4-b]pyridazin-7-ones." The Journal of organic chemistry vol. 71,6 (2006): 2293-301. doi: https://doi.org/10.1021/jo052329e
Dang TT, Albrecht U, Gerwien K, Siebert M, Langer P. One-pot cyclizations of dilithiated oximes and hydrazones with epibromohydrin. Efficient synthesis of 6-hydroxymethyl-5,6-dihydro-4H-1,2-oxazines and oxazolo[3,4-b]pyridazin-7-ones. J Org Chem. 2006 Mar 17;71(6):2293-301. doi: 10.1021/jo052329e. PMID: 16526776.
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J Org Chem. 2006 Mar 17;71(6):2293-301. doi: 10.1021/jo052329e.

One-pot cyclizations of dilithiated oximes and hydrazones with epibromohydrin. Efficient synthesis of 6-hydroxymethyl-5,6-dihydro-4H-1,2-oxazines and oxazolo[3,4-b]pyridazin-7-ones.

The Journal of organic chemistry

Tuan Thanh Dang, Uwe Albrecht, Katrin Gerwien, Melanie Siebert, Peter Langer

Affiliations

  1. Leibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock, Germany.

PMID: 16526776 DOI: 10.1021/jo052329e

Abstract

The one-pot cyclization of dilithiated oximes with epibromohydrin provided a convenient and regioselective approach to 6-hydroxymethyl-5,6-dihydro-4H-1,2-oxazines. The reaction of the latter with phosphorus tribromide resulted in a Beckmann rearrangement and formation of 5-bromomethyl-2-iminotetrahydrofurans. The reaction of dilithiated hydrazones with epibromohydrin afforded oxazolo[3,4-b]pyridazin-7-ones, which were formed by a novel domino cyclization.

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