Synthesis 2019; 51(06): 1383-1390
DOI: 10.1055/s-0037-1610845
paper
© Georg Thieme Verlag Stuttgart · New York

The Easy Approach to N-Hydroxy-N-cycloalkenylamides through Nitrosocarbonyl Ene Reactions to Cycloalkenes: Valuable Compounds for Antiviral Syntheses

Karzan Khaleel Hameed
a  Salahaddin University – Erbil, Department of Chemistry, College of Science, Erbil, Iraq
,
Ahmed Anwar Amin
a  Salahaddin University – Erbil, Department of Chemistry, College of Science, Erbil, Iraq
,
Faiq H. S. Hussain
b  Research Center-Ishik University, Erbil, Kurdistan Region, Iraq
,
Misal Giuseppe Memeo
c  Dipartimento di Chimica, Università degli Studi di Pavia, Viale Taramelli 12, 27100 – Pavia, Italy   Email: paolo.quadrelli@unipv.it
,
Mattia Moiola
c  Dipartimento di Chimica, Università degli Studi di Pavia, Viale Taramelli 12, 27100 – Pavia, Italy   Email: paolo.quadrelli@unipv.it
,
c  Dipartimento di Chimica, Università degli Studi di Pavia, Viale Taramelli 12, 27100 – Pavia, Italy   Email: paolo.quadrelli@unipv.it
› Author Affiliations
Financial support: University of Pavia, MIUR (PRIN 2011, CUP: F11J12000210001) and COST Action CM1004. We also thank ‘VIPCAT – Value Added Innovative Protocols for Catalytic Transformations’ project (CUP: E46D17000110009) for valuable financial support.
Further Information

Publication History

Received: 06 September 2018

Accepted after revision: 22 October 2018

Publication Date:
21 November 2018 (eFirst)

Abstract

An easy approach to N-hydroxy-N-cycloalkenylamides, ene adducts of cyclic alkenes of different sizes, is presented. The products can be obtained both through the thermal generation of the nitrosocarbonyl intermediates and via the photochemical fragmentation of the Wieland heterocycle, this being the mildest way to generate these fleeting species, also affording the best results so far in terms of chemical yields. The use of the ene reaction for the synthesis of biologically active molecules represents an interesting and valuable aspect of modern organic synthesis, and this is the strategy proposed as a remarkable alternative to current methods.

Supporting Information

 
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