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Electrophile‐Mediated Reactions of Functionalized Propargylic Substrates
Author(s) -
Urbanaitė Aurelija,
Jonušis Mantas,
Bukšnaitienė Rita,
Balkaitis Simonas,
Čikotienė Inga
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501063
Subject(s) - chemistry , electrophile , regioselectivity , chalcogen , oxocarbenium , substrate (aquarium) , halogen , combinatorial chemistry , organic chemistry , stereochemistry , medicinal chemistry , catalysis , oceanography , alkyl , nucleophile , geology
Metal‐free halogen, chalcogen, or oxocarbenium ion mediated yne‐carbonyl or yne‐thioxo transformations of a range of N ‐ and O ‐propargylic compounds have been studied. This investigation has led to the development of a mild, economic, and effective method for the synthesis of functionalized 4 H ‐1,3‐oxazines, 4 H ‐1,3‐thiazines, 4,5‐dihydrothiazoles, and α‐substituted enones. The structure of the propargylic substrate and the nature of electrophile influence both the outcome and regioselectivity of processes.