Banca de DEFESA: IGOR SANDE DE SANTANA

Uma banca de DEFESA de MESTRADO foi cadastrada pelo programa.
STUDENT : IGOR SANDE DE SANTANA
DATE: 02/04/2024
TIME: 09:00
LOCAL: Sala de seminários do IQ
TITLE:

Mechanochemistry and telescopic synthesis as synthetic strategies to obtain benzoheterocycles, α-naphthols and new 1,2-naphthoquinone derivatives

KEY WORDS:

polyazaheterocycles, sustainable synthesis, benzofuran

PAGES: 138
BIG AREA: Ciências Exatas e da Terra
AREA: Química
SUBÁREA: Química Orgânica
SPECIALTY: Síntese Orgânica
SUMMARY:

The telescopic approach within organic synthesis has been
used as an allied tool to achieve synthetic planning
increasingly sustainable, within the concept and parameters of chemical
green. This strategy, in addition to offering a reduction in unit stages of
purification of intermediates, and consequently the generation of waste,
can also simplify the practical aspects of a synthesis and has already been
used by the pharmaceutical industry. Furthermore, mechanochemistry also
has been acting within organic synthesis with an important role in
more sustainable synthetic planning, in addition to enabling access to
reactivity and non-trivial reaction conditions employing methods
conventional. In this work, a synthesis method was developed for the
obtaining benzoheterocycles (14-72%), 4-acetoxinphthalenes (30-65%) and 4H-
quinolizin-4-one (88%) from Wittig olefination and acylation reactions
from Friedel-Crafts, combined in a two-pot telescopic approach,
employing mechanochemistry and microwave heating respectively.
The advantage offered by mechanochemistry made it possible to carry out
olefination in the absence of solvent and in a non-inert atmosphere, bypassing the
solvent drying steps and purging of the reaction system with
gases. The developed method uses half-esters as an intermediate
itaconic (41-87%), which were also isolated and characterized,
originating from the olefination reaction using α-triphenylphosphoranylidene-
monomethyl succinate against aldehydes in mechanochemistry. Furthermore, the
Synthetic potential of itaconic half-esters was explored in the synthesis of 9-
methyl nitro-2,3-dihydrobenzo[b]oxapin-2-one-4-carboxylate (70%) and 2,3-
methyl dihydro-1H-benzo[b]azepin-2-one-4-carboxylate (71%), demonstrating
be a versatile synthetic intermediate by enabling access to molecules with
structural diversity. From the synthesized 4-acetoxinphthalenes,
possible to access α-naphthols (81-98%), which, together with other analogues of
naphthols, were investigated against hypervalent iodine reagents for the
synthesis of new analogues and derivatives of naphthoquinones using the
telescopic approach, making it possible to access new benzo[a]phenazines (35-
85%), pyrido[2,3-a]phenazines (32-93%) and oxazoles (36-56%).

COMMITTEE MEMBERS:
Presidente - 1215450 - SILVIO DO DESTERRO CUNHA
Interno - 1507716 - MAURICIO MORAES VICTOR
Interno - 2166886 - ANDRE ALEXANDRE VIEIRA
Externa à Instituição - SABRINA TEIXEIRA MARTINEZ - UFRJ
Externo à Instituição - JULIO CEZAR PASTRE - UNICAMP