Synthesis of 3-aryl/benzyl-4,5,6,6a-tetrahydro-3aH-pyrrolo[3,4-d]isoxazole derivatives: a comparison between conventional, microwave-assisted and flow-based methodologies

Sabrina Castellano; Lucia Tamborini; Monica Viviano; Andrea Pinto; Gianluca Sbardella; Paola Conti

doi:10.1021/jo1014323

Synthesis of 3-aryl/benzyl-4,5,6,6a-tetrahydro-3aH-pyrrolo[3,4-d]isoxazole derivatives: a comparison between conventional, microwave-assisted and flow-based methodologies

J Org Chem. 2010 Nov 5;75(21):7439-42. doi: 10.1021/jo1014323.

Authors

Sabrina Castellano¹, Lucia Tamborini, Monica Viviano, Andrea Pinto, Gianluca Sbardella, Paola Conti

Affiliation

¹ Dipartimento di Scienze Farmaceutiche, Università degli Studi di Salerno, Via Ponte Don Melillo, 84084 Fisciano, Italy.

PMID: 20882999
DOI: 10.1021/jo1014323

Abstract

Two modern synthetic technologies to perform 1,3-dipolar cycloaddition reactions were compared. This study puts in evidence the power of microwave-assisted and flow-based methodologies compared to the conventional one in terms of reaction time and yield, and demonstrates the potential of flow chemistry in terms of time, automation, and scaling up opportunities.

Publication types

Comparative Study
Research Support, Non-U.S. Gov't

MeSH terms

Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis
Bridged Bicyclo Compounds, Heterocyclic / chemistry
Isoxazoles / chemical synthesis*
Isoxazoles / chemistry*
Microwaves*
Nitriles / chemistry
Pyrroles / chemistry

Substances

Bridged Bicyclo Compounds, Heterocyclic
Isoxazoles
Nitriles
Pyrroles
pyrroline