Issue 53, 2022
From the journal:

RSC Advances

Synthesis of fully functionalised spiropyran pyrazolone skeletons via a formal [4 + 2] cascade process using β-nitro-styrene-derived MBH-alcohols†

Yeruva Pavankumar Reddya  and  Shaik Anwar ORCID logo *a  

* Corresponding authors

a Department of Chemistry, School of Applied Sciences and Humanities, Vignan's Foundation for Science Technology and Research-VFSTR (Deemed to be University), Vadlamudi-522213, Guntur, Andhra Pradesh, India
E-mail: shaikanwarcu@gmail.com, drsa_sh@vignan.ac.in
Web: http://www.vignan.ac.in/bshanwar.php
Tel: +91-8632344700

Abstract

An efficient protocol was established to construct spiro pyrazolone tetrahydropyran scaffolds at ambient temperature under metal-free conditions. The reaction proceeded via formal [4 + 2] cyclisation of trans-β-nitro-styrene-derived Morita–Baylis–Hillman (MBH) alcohol with α-arylidene pyrazolone. The reaction followed an oxa-Michael/Michael cascade pathway, resulting in the formation of new C–C and C–O bonds. Organocatalytic synthesis of spiropyrazolones using quinine-derived catalyst resulted in 94% enantiomeric excess (ee) and excellent (>20 : 1) diastereoselectivity.

Graphical abstract: Synthesis of fully functionalised spiropyran pyrazolone skeletons via a formal [4 + 2] cascade process using β-nitro-styrene-derived MBH-alcohols

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Article information

DOI
https://doi.org/10.1039/D2RA06076K
Article type
Paper
Submitted
27 Sep 2022
Accepted
12 Nov 2022
First published
02 Dec 2022
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2022,12, 34634-34638

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Synthesis of fully functionalised spiropyran pyrazolone skeletons via a formal [4 + 2] cascade process using β-nitro-styrene-derived MBH-alcohols

Y. P. Reddy and S. Anwar, RSC Adv., 2022, 12, 34634 DOI: 10.1039/D2RA06076K

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