Morita-Baylis-Hillman adducts as building blocks of heterocycles: a simple approach to 4-substituted pyrazolones, and mechanism investigation via ESI-MS(/MS)

Author(s)

Barcelos, Rosimeire C. ^[1] ; Zeoly, Lucas A. ^[1] ; Rodrigues, Jr., Manoel T. ^[1] ; Ferreira, Bruno R. V. ^[2] ; Eberlin, Marcos N. ^[2] ; Coelho, Fernando ^[1]

Affiliation

^[1] Univ Estadual Campinas, Lab Synth Nat Prod & Drugs, BR-13083970 Campinas, SP - Brazil

^[2] Univ Estadual Campinas, Lab ThoMSon Mass Spectrometry, BR-13083970 Campinas, SP - Brazil

• Document type: Journal article
• Source: MONATSHEFTE FUR CHEMIE; v. 146, n. 9, p. 1557-1570, SEP 2015.
• Web of Science Citations: 4

Abstract

We describe herein an efficient approach for the preparation of 4-substituted 2,3-dihydro-1H-pyrazol-3-ones starting from Morita-Baylis-Hillman adducts. These heterocycles were obtained in two or three steps as single isomers with moderate to good overall yields. One efficient and alternative methodology for the synthesis of alpha-methyl-beta-ketoesters is also reported (up to 91 % yield). Additionally, the mechanism of formation of pyrazolones was investigated employing ESI-MS/MS reaction monitoring. (AU)

• FAPESP's process: 12/24783-1 - Morita-Baylis-Hillman in medicinal chemistry: synthesis and neuroprotective, antimicrobial and antitumoral biological evaluations of new heterocycles, oximes and nitrones
• Grantee: Rosimeire Coura Barcelos
• Support Opportunities: Scholarships in Brazil - Post-Doctoral