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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

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

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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]
Total Authors: 5
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
Total Affiliations: 2
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 type: Regular Research Grants
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 type: 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 type: Scholarships in Brazil - Doctorate