Unexpected highly regioselective macrocyclization of o-allylic N-carbonyl substituted anilines

Autor:	José L. García-Navío, Juan J. Vaquero, Carlos Lamas, Javier Agejas, Francisca Delgado
Rok vydání:	2002
Předmět:	Allylic rearrangement Chemistry Organic Chemistry Drug Discovery Organic chemistry Regioselectivity Biochemistry
Zdroj:	Tetrahedron Letters. 43:8025-8027
ISSN:	0040-4039
DOI:	10.1016/s0040-4039(02)01974-3
Popis:	An unexpected bromocyclocarbamoylation of o -allylic N -BOC-anilines has been observed producing 2-oxo-3,1-benzoxazocine derivatives through an 8- endo - trig process, which on heating ring-transformed into a [6.5.5] tricyclic fused oxazolidinone compounds. A mixture of both heterocycles was obtained when the starting N -BOC anilines were heated with NBS in THF. The process seems to be general for related N -carbonyl substituted anilines.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::f8ef12c9d93f2fb6488a06cb9eb11d4b https://doi.org/10.1016/s0040-4039(02)01974-3 Zobrazit plný text záznamu Full Text from ScienceDirect