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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.)

Base-Controlled Regioselective Functionalization of Chloro-Substituted Quinolines

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Author(s):
Murie, Valter E. [1] ; Nishimura, Rodolfo H. V. [2, 1] ; Rolim, Larissa A. [3] ; Vessecchi, Ricardo [2] ; Lopes, Norberto P. [1] ; Clososki, Giuliano C. [2, 1]
Total Authors: 6
Affiliation:
[1] Univ Sao Paulo, Fac Ciencias Farmaceut Ribeirao Preto, Nucleo Pesquisas Prod Nat & Sintet, Ave Cafe S-N, BR-14040903 Ribeirao Preto, SP - Brazil
[2] Univ Sao Paulo, Fac Filosofia Ciencias & Letras Ribeirao Preto, Dept Quim, Ave Bandeirantes 3900, BR-14040901 Ribeirao Preto, SP - Brazil
[3] Univ Fed Vale Sao Francisco, Colegiado Ciencias Farmaceut, Ave Jose de Sa Manicoba S-N, BR-56304205 Petrolina, PE - Brazil
Total Affiliations: 3
Document type: Journal article
Source: Journal of Organic Chemistry; v. 83, n. 2, p. 871-880, JAN 19 2018.
Web of Science Citations: 6
Abstract

We prepared a number of di- and trifunctionalized quinolines by selective metalation of chloro-substituted quinolines with metal amides followed by reaction with different electrophiles. Metalation of the C-3 position of the quinolinic ring with lithium diisopropylamide at -70 degrees C is easy to achieve, whereas reaction with lithium magnesium and lithium zinc amides affords C-2 or C-8 functionalized derivatives in a regioselective fashion. These complementary methods could be rationalized by DFT calculations and are convenient strategies toward the synthesis of bioactive quinoline derivatives such as chloroquine analogues. (AU)

FAPESP's process: 15/21364-6 - Applicantion of organometallic reagents in the directed functionalization of quinolines aimming the synthesis of medicinal interest compounds
Grantee:Valter Eduardo Murie
Support type: Scholarships in Brazil - Doctorate
FAPESP's process: 15/01466-9 - Directed functionalization of quinazolines and quinazolinones aiming the synthesis of bioactive substances
Grantee:Rodolfo Hideki Vicente Nishimura
Support type: Scholarships in Brazil - Doctorate
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