10.1002/chem.201901111
Chemistry - A European Journal
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63/27) difficult to separate. With TFAA, 30 was obtained
however with cis/trans (48/52) from which we were able to
isolate the cis isomer determined by Noesy measurements.
Havre-Normandie’ from the COmuE-NU and HEI from Lille for
the financial help of this work. The letter was created also with
the support of the MŠVVaŠ of the Slovak Republic within the
Research and Development Operational Programme for the
project "University Science Park of STU Bratislava" (ITMS
project no. 26240220084) cofounded by the European Regional
Development Fund.
Conclusions
In summary, unlike the existing and rare methods for two-steps
or one-step Morin rearrangement, by using the PIDA/I2
combination for the first time we have developed a ‘one-step’
approach from N,S-acetals without need of the formation of the
sulfoxide. This provides an easy and efficient access to a large
assembly of 1,4-thiazines fused or not to pyrrolidones or
isoindolones, with total regiosectivity where this is the case, and
Conflict of interest
The authors declare no conflict of interest.
Keywords: Morin rearrangement • Domino transformation • 1,3-
Thiazolidines • 1,4-Thiazines • PIDA/I2 combination • Oxidative
methylene insertion
in good yields. When another proton is present at endocy
-
position of the sulfur atom, typically in pyrrolidone or piperidone
series, the expected Morin products were accompanied with the
over oxidizing compounds in moderate to good yields. As an
application of this approach, a dehydroxylated natural product
analogue and other intermediates available for post
functionalization at different positions necessary for further
QSAR study were reported.
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The authors are grateful to MESRS (Ministère de
l’Enseignement Supérieur & de la Recherche Scientifique) for
the Graduate Fellowship awarded to F. D and ‘Université Le
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