Synthesis of Spiro [furan-2, 1′-isoindolin]-3′-ones from 2-(4-Hydroxybut-1-yn-1-yl) benzonitriles and Aryl Aldehydes under the Action of Triflic Acid

S Shit, SK Bora, AK Sahu, AK Saikia - The Journal of Organic …, 2022 - ACS Publications
The synthesis of spiro [furan-2, 1′-isoindolin]-3′-ones from 2-(4-hydroxybut-1-yn-1-yl)
benzonitriles and aryl aldehydes is demonstrated. It involves the initial formation of …

Regio- and Chemoselective Synthesis of 3-(Dihydrofuran-3(2H)-ylidene)isobenzofuran-1(3H)-imines via Tandem Alkynyl Prins- and Intramolecular Oxycyclization …

S Shit, BK Behera, S Biswas… - The Journal of Organic …, 2023 - ACS Publications
A metal-free Lewis acid-initiated protocol for the synthesis of highly substituted 3-
(dihydrofuran-3 (2 H)-ylidene) isobenzofuran-1 (3 H)-imines from 2-(4-hydroxybut-1-yn-1-yl) …

Brønsted acid catalyzed carbocyclizations involving electrophilic activation of alkynes

P Hermange, J Gicquiaud, M Barbier, A Karnat… - …, 2022 - thieme-connect.com
This review focuses on the carbocyclization reactions of alkyne-containing substrates
catalyzed by Brønsted acids. The electrophilic activation occurs either by direct protonation …

Nitrogen-interrupted halo-Prins/halo-Nazarov fragment coupling cascade for the synthesis of indolines

A Milosavljevic, C Holt, AJ Frontier - Chemical Science, 2023 - pubs.rsc.org
The nitrogen-interrupted Nazarov cyclization can be a powerful method for the
stereocontrolled synthesis of sp3-rich N-heterocycles. However, due to the incompatibility …

Alkynyl Prins carbocyclization cascades for the synthesis of linear-fused heterocyclic ring systems

JJ Hernandez, AJ Frontier - Chemical Science, 2022 - pubs.rsc.org
We report a Brønsted acid-catalyzed carbocyclization cascade, featuring condensation of an
alcohol/sulfonamide with an aldehyde followed by an intramolecular three-component …

Synthetic applications of Prins cyclization in natural product syntheses

K Tadiparthi, A Roy, R Sakirolla… - The Chemical …, 2022 - Wiley Online Library
The natural products having tetrahydropyran unit with multiple chiral centers serve as
magnificent building blocks for various active pharmaceutical ingredients (APIs).'Prins …

Synthesis of Spirocyclic Isoindolones Using an Alkynyl aza-Prins/Oxidative halo-Nazarov Cyclization Sequence

JJ Hernandez, AJ Frontier - Organic Letters, 2021 - ACS Publications
In this report, we describe an alkynyl halo-aza-Prins cyclization of 3-hydroxyisoindolones to
prepare aza-Prins products. These Prins adducts undergo oxidation at the 3-isoindolone …

Alkynyl Halo-Aza-Prins Annulative Couplings

JJ Hernandez, AP Lawrie… - The Journal of Organic …, 2023 - ACS Publications
This article is a comprehensive report describing our studies in the field of aza-alkynyl Prins
chemistry, comparing and contrasting the different reaction partners and reactivities …

Leveraging Alkyne–Oximium Cyclization for the Stereoselective Synthesis of Isoxazolidine

SJ Gharpure, J Pal, KC Pansuriya - Organic Letters, 2022 - ACS Publications
A TMSOTf-mediated highly diastereoselective synthesis of isoxazolidine bearing three
contiguous stereocenters is described. This method utilizes O-propargyl hydroxylamines as …

Leveraging cascade alkynyl Prins cyclization towards the stereoselective synthesis of spiro-furan quinazolinone scaffolds

S Biswas, S Shit, BK Behera, AK Sahu… - Chemical …, 2023 - pubs.rsc.org
A TfOH-promoted, metal-free protocol has been unveiled for the synthesis of spiro-furan
quinazolinones employing alkynol urea derivatives utilizing alkynyl Prins cyclization …