| Full text | |
| Author(s): |
dos Santos, Thiago
[1]
;
Orenha, Henrique P.
[1]
;
Murie, Valter E.
[1]
;
Vessecchi, Ricardo
[1]
;
Clososki, Giuliano C.
[1]
Total Authors: 5
|
| Affiliation: | [1] Univ Sao Paulo, Fac Ciencias Farmaceut Ribeirao Preto, Dept Ciencias BioMol, BR-14040903 Ribeirao Preto, SP - Brazil
Total Affiliations: 1
|
| Document type: | Journal article |
| Source: | ORGANIC LETTERS; v. 23, n. 19, p. 7396-7400, OCT 1 2021. |
| Web of Science Citations: | 0 |
| Abstract | |
We have accomplished regioselective deprotometalation of aromatic and heteroaromatic nitriles via (TMP)(2)Zn center dot 2MgCl(2)center dot 2LiCl and TMPMgCl center dot LiCI (TMP = 2,2,6,6-tetramethylpiperidyl) with the exploration of new and scarcely investigated metalation positions. Regioselectivity was rationalized by DFT calculations. The quenching of the generated organozinc and organomagnesium intermediates with various electrophiles gave access to 47 highly functionalized nitriles with yields up to 95%. Additionally, we report a difunctionalization strategy and the use of functionalized nitriles as building blocks to construct relevant heterocycles. (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 Opportunities: | Scholarships in Brazil - Doctorate |
| FAPESP's process: | 18/14150-8 - Selective aromatic functionalization: Methodological Studies and new applications in the synthesis of BIOATIVE compounds |
| Grantee: | Giuliano Cesar Clososki |
| Support Opportunities: | Regular Research Grants |
| FAPESP's process: | 15/01017-0 - Multi-use instrument approved and awarded in the project 2013/50228-8, name of instrument: ultra-performance liquid chromatograph coupled with a high resolution mass spectrometer |
| Grantee: | Roberto Gomes de Souza Berlinck |
| Support Opportunities: | Multi-user Equipment Program |