ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

A simple and efficient route to pyrazole-based dihydrofuranones via lactonization approach

Shubham Sharma, Virender Singh, Vinod Kumar Vashistha, Manpreet Singh, and Ashutosh Sharma

Department of Chemistry, GLA University, Mathura, India

E-mail: rajshubh.9557@gmail.com

Received: 12 August 2023  Accepted: 13 November 2023

Abstract:

The diastereoselective synthesis of novel pyrazole and dihydrofuranone-based molecular hybrids has been unfolded through the development of a straightforward tandem strategy. The indium-mediated Barbier-type allylation reaction was followed by an in situ lactonization approach. No additives were required for this transformation, and high yields of dihydrofuranone derivatives were obtained with syn-stereochemistry. The current protocol provides a number of benefits, including a one-pot procedure, high diastereoselectivity, a broad substrate scope, and high yields of the desired products.

Keywords: Pyrazole C-3/C-5 carbaldehydes; Dihydrofuranones; Barbier-type allylation; Lactonization; Indium-mediated; Pharmaceutical importance

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-023-03257-6

Chemical Papers 78 (4) 2519–2534 (2024)