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Selenoacetalyzation of 4‐Formylpyrazoles in the Presence of Trimethylchlorosilane

Selenoacetalyzation of 4‐Formylpyrazoles in the Presence of Trimethylchlorosilane ABSTRACT The reaction of 3,5‐dimethyl‐4‐formylpyrazoles, bearing various substituents at N‐1 atom, with propane‐1,3‐diselenol and 2‐hydroxypropane‐1,3‐diselenol in the presence of ТМSCl proceeds without heating to chemoselectively give hitherto unknown 2‐(pyrazol‐4‐yl)‐1,3‐diselenane hydrochlorides in high yields. The latter are easily transformed to the corresponding free bases—2‐(pyrazol‐4‐yl)‐1,3‐diselenanes. The 15N chemical shifts of the pyrazole ring in 2‐(pyrazol‐4‐yl)‐1,3‐diselenanes obtained by 2D HMBC‐gp (15N‐1H) technique are indicative of the N‐2 atom protonation in hydrochlorides. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Heteroatom Chemistry Wiley

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References (21)

Publisher
Wiley
Copyright
Copyright © 2013 Wiley Periodicals, Inc.
ISSN
1042-7163
eISSN
1098-1071
DOI
10.1002/hc.21113
Publisher site
See Article on Publisher Site

Abstract

ABSTRACT The reaction of 3,5‐dimethyl‐4‐formylpyrazoles, bearing various substituents at N‐1 atom, with propane‐1,3‐diselenol and 2‐hydroxypropane‐1,3‐diselenol in the presence of ТМSCl proceeds without heating to chemoselectively give hitherto unknown 2‐(pyrazol‐4‐yl)‐1,3‐diselenane hydrochlorides in high yields. The latter are easily transformed to the corresponding free bases—2‐(pyrazol‐4‐yl)‐1,3‐diselenanes. The 15N chemical shifts of the pyrazole ring in 2‐(pyrazol‐4‐yl)‐1,3‐diselenanes obtained by 2D HMBC‐gp (15N‐1H) technique are indicative of the N‐2 atom protonation in hydrochlorides.

Journal

Heteroatom ChemistryWiley

Published: Nov 1, 2013

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