TMSOTf-mediated approach to 1,3-oxazin-2-one skeleton through one-pot successive reduction-[4 + 2] cyclization process of imides with ynamides

Autor:	Xun Sun, Mei-Lin Tang, Yongxi Liang, Zhi-Peng Huo, Chen-Chen Zhang
Rok vydání:	2021
Předmět:	Reduction (complexity) Bicyclic molecule 010405 organic chemistry Chemistry Organic Chemistry Drug Discovery 010402 general chemistry Ring (chemistry) 01 natural sciences Biochemistry Combinatorial chemistry 0104 chemical sciences
Zdroj:	Tetrahedron Letters. 68:152946
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2021.152946
Popis:	A one-pot approach to access functionalized 1,3-oxazin-2-one skeleton has been developed through successive reduction and subsequent [4 + 2] cyclization process of N-Boc lactams with ynamides by TMSOTf. As a result, a number of five to seven membered ring fused bicyclic [1,2-c] [1] , [3] oxazin-1-ones 12a-m and tricyclic derivatives 13a-f were obtained in moderate to excellent yields with excellent regioselectivities. Moreover, linear N-Boc amides 9a-e were also amenable to this transformation, and the desired 3,4-dihydro-1,3-oxazin-2-ones 14a-m were readily achieved in moderate yields with excellent regioselectivities.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::bd11513588c2346bdc463339040ba369 https://doi.org/10.1016/j.tetlet.2021.152946 Zobrazit plný text záznamu Full Text from ScienceDirect