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One‐pot three‐component preparation of novel selenium‐containing spiroketals
Author(s) -
Braverman Samuel,
Cherkinsky Marina,
Kalendar Yuliya,
Gottlieb Hugo E.,
Mats Ella Meltzer,
Gruzman Arie,
Goldberg Israel,
Sprecher Milon
Publication year - 2013
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.2952
Subject(s) - chemistry , selenium , acetone , yield (engineering) , propargyl , stereospecificity , regioselectivity , ketone , organic chemistry , catalysis , materials science , metallurgy
The one‐pot three‐component preparation of novel selenium‐containing spiroketals with potential biological activity is described. When in situ prepared selenium dichloride is reacted with either propargyl or homopropargyl alcohols in the presence of acetone, two competitive reactions take place, namely 1,2‐addition to the triple bond with the formation of the corresponding functionalized divinyl selenides in a completely regio‐ and stereospecific manner and selenylation at the α‐position of the ketone, leading to the novel selenium‐containing spiroketals. An alternative approach to the synthesis of the selenium‐containing spiroketals with substantial increase of the chemical yield involves the reaction of alkynyl acetals with SeCl 2 . The structure of ( 4E,11E )‐4,11‐bis(chloromethylene)‐1,8‐dioxa‐5,12‐diselenaspiro[6.6]tridecane was unambiguously confirmed by X‐ray analysis. These novel selenium‐containing spiroketals were tested for regulation of glucose uptake in L6 myotubes. Copyright © 2012 John Wiley & Sons, Ltd.