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Selenium‐Containing Heterocycles from Isoselenocyanates: Synthesis of 1,3‐Selenazinane and 1,3‐Selenazinanone Derivatives
Author(s) -
Sommen Geoffroy L.,
Linden Anthony,
Heimgartner Heinz
Publication year - 2007
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200790051
Subject(s) - chemistry , ketene , electrophile , hemiacetal , yield (engineering) , selenium , aryl , stereochemistry , medicinal chemistry , organic chemistry , catalysis , materials science , alkyl , metallurgy
The reaction of the intermediate ketene N,Se‐hemiacetal 3 , prepared from cyanomethylene derivatives 1 by treatment with Et 3 N and aryl isoselenocyanates 2 , with bis‐electrophiles 6, 7, 9 , and 11 in DMF affords tetrahydro‐1 H ‐1,3‐selenazine (=1,3‐selenazinane) derivatives 8, 10 , and 12 in good yield ( Scheme 2 and Tables 1–3 ). Chemical and spectroscopic evidence for the structures of the new compounds are described. The structures of 8d and 12e are established by X‐ray crystallography ( Figs. 1 and 2 ).