Synthesis of Selenazoles by in Situ Cycloisomerization of Propargyl Selenoamides Using Oxygen–Selenium Exchange Reaction

Autor:	Chiara Pizzo, Graciela Mahler
Rok vydání:	2014
Předmět:	In situ Molecular Structure Cyanide Organic Chemistry chemistry.chemical_element Oxygen Catalysis Selenium chemistry.chemical_compound Cycloisomerization Pargyline chemistry Cyclization Reagent Propargyl Organic chemistry Selenium Compounds Derivative (chemistry)
Zdroj:	The Journal of Organic Chemistry. 79:1856-1860
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo402661b
Popis:	Herein, we describe an approach toward selenazole preparation based on the cycloisomerization of propargyl selenoamides. The selenoamides were synthesized in situ using the Ishihara reagent with spontaneous cyclization to form the 2,5-disubstituted selenazoles. Heterocylcles 9a-j were prepared using readily available starting materials, and yields ranged from moderate to good (20-80%). Methylselenazole 9a could be transformed into a bromomethyl derivative 13 using NBS. The intermediate 13 would provide a more versatile building block for further derivatizations, e.g., the cyanide 14.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::8e4ddc4bfd0dbec13260db58cccb6135 https://doi.org/10.1021/jo402661b Zobrazit plný text záznamu