Selective functionalization of cyano-phenyl-2-oxazolines using TMPMgCl center dot LiCl

Author(s)

Bozzini, Leandro A. ^[1] ; Batista, Joao H. C. ^[1] ; de Mello, Murilo B. M. ^[1] ; Vessecchi, Ricardo ^[2] ; Clososki, Giuliano C. ^{[2, 1]}

Affiliation

^[1] Univ Sao Paulo, Fac Farmaceut Ribeirao Preto, Nucleo Pesquisas Prod Nat & Sintet, Av Cafe S-N, BR-14040903 Ribeirao Preto, SP - Brazil

^[2] Univ Sao Paulo, Fac Filosofia Ciencias & Letras Ribeirao Preto, Dept Quim, Av Bandeirantes 3900, BR-14040901 Ribeirao Preto, SP - Brazil

• Document type: Journal article
• Source: Tetrahedron Letters; v. 58, n. 44, p. 4186-4190, NOV 1 2017.
• Web of Science Citations: 9

Abstract

Metalated phenyl-2-oxazolines bearing cyano groups can be selectively obtained through the reaction of TMPMgCl center dot LiCl with the appropriate substrate. Subsequent reaction with different electrophiles furnished the functionalized derivatives in good yields. Density functional theory (DFT) calculations were performed to evaluate the influence of the ring substituents on the acidity of the aromatic hydrogens. Application to the synthesis of novel functionalized phthalides illustrates the great potential of the methodology to the synthesis of bioactive compounds. (C) 2017 Elsevier Ltd. All rights reserved. (AU)

• FAPESP's process: 15/12811-9 - DIRECTED FUNCTIONALIZATION OF ARENES AND HETEROARENES AIMIMNG THE SYNTHESIS OF SUBSTANCES OF MEDICINAL INTEREST
• Grantee: Giuliano Cesar Clososki
• Support Opportunities: Regular Research Grants
• FAPESP's process: 11/12589-3 - Application of New Organometallic Reagents in Synthesis of Bioactive Substance
• Grantee: João Henrique Carvalho Batista
• Support Opportunities: Scholarships in Brazil - Doctorate
• FAPESP's process: 14/23604-1 - Computational chemistry: a tool to studies of mass spectrometry, reactivity and fragmentation/reaction mechanisms of organic compounds
• Grantee: Ricardo Vessecchi Lourenço
• Support Opportunities: Regular Research Grants