Rh(II)/Mg(OtBu)2-Catalyzed Tandem One-Pot Synthesis of 1,4-Oxazepines and 1,4-Oxazines from N-Sulfonyl-1,2,3-triazoles and Glycidols
- 등재 SCIE, SCOPUS
- 발행기관 American Chemical Society
- 발행년도 2016
- 총서유형 Journal
- URI http://www.dcollection.net/handler/ewha/000000139414
- 본문언어 영어
- Published As http://dx.doi.org/10.1021/acs.orglett.6b03328
- 저작권 이화여자대학교 논문은 저작권에 의해 보호받습니다.
초록/요약
A novel, one-pot route for the synthesis of nonaromatic ring-fused 1,4-oxazepines and 1,4-oxazines has been developed. The reaction features a sequential rhodium(II)-catalyzed reaction of N-sulfonyl-1,2,3-triazoles with glycidols, followed by a regioselective Lewis acid Mg(OtBu)2-catalyzed intramolecular ring-opening reaction. It has been found that the regioselectivity in the epoxide ring-opening was largely determined by the substituents on the glycidols. Thus, substituted glycidols (R2 ≠ H) afforded seven-membered oxazepine derivatives selectively, while unsubstituted glycidols (R2 = H) afforded six-membered oxazine derivatives. Plausible reaction pathways are elucidated and supported by experiments with several glycidols bearing different substituents around the epoxide functionality. © 2016 American Chemical Society.
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