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Thiazole constrained analogues of the thevinones: synthesis and structure
Author(s) -
Sipos Attila,
Skaliczki Tímea,
Berényi Sándor,
Antus Sándor
Publication year - 2009
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.2447
Subject(s) - chemistry , thiazole , methyl vinyl ketone , stereoselectivity , yield (engineering) , ring (chemistry) , cycloaddition , ketone , two dimensional nuclear magnetic resonance spectroscopy , stereochemistry , proton nmr , nuclear magnetic resonance spectroscopy , combinatorial chemistry , organic chemistry , catalysis , materials science , metallurgy
A simple synthesis of ring‐constrained endoethenomorphinans possessing 2′‐substituted thiazole ring 4–6 has been achieved by regio‐ and stereoselective Diels–Alder reaction of thiazolomorphinandienes 1–3 and methyl vinyl ketone in high yield (72, 64 and 87%, respectively). The structure of cycloaddition products was determined by high resolution mass spectrometry (HRMS), IR, 1D and 2D NMR techniques. Double‐pulsed field gradient spin‐echo–nOe and HMBC were found to be particularly powerful and indispensable tools in the exact structural elucidation of the presented new class of spatially constrained thevinones. Copyright © 2009 John Wiley & Sons, Ltd.