SYNTHESIS OF N-HETEROCYCLES VIA PALLADIUM-CATALYZED REDUCTIVE CYCLIZATION REACTIONS OF NITROARENES AND NITROALKENES USING FORMIC ACID DERIVATIVES AS CO SURROGATES

The reductive cyclization reaction of nitroarenes to produce N-heterocycles has been ‎investigated for more than four decades using CO as a cheap reductant, but it is still a ‎fascinating area for research and advancements. On the other hand, using toxic CO gas is ‎accompanied by many disadvantages. Thus, the thesis focuses on the use of phenyl formate and ‎formic acid as cheap, affordable, efficient and safe in-situ CO surrogates for the reductive ‎cyclization of various nitroarenes. Notably, in most cases, the isolated yield of the desired ‎heterocycle was higher than those previously obtained for the same reaction when gaseous CO ‎had been employed, which indicates that the use of these surrogates should not necessarily be ‎considered a second choice when the use of CO gas is not possible. A cheap thick-walled glass ‎‎“pressure tube” can be used instead of less-available autoclaves.‎

Grantor dc:publisher

Università degli Studi di Milano

Year dc:date

2024

Author dc:creator

• ABDELLATIF, MANAR AHMED FOUAD

Contributors dc:contributor

• tutor: F. A. C. Ragaini ; coordinator: D. Passarella
• M.A.F. Abdellatif
• RAGAINI, FABIO ATTILIO CIRILLO
• PASSARELLA, DANIELE

• Reductive Cyclization
• Reduction
• Palladium
• Catalysi
• Heterocycle
• CO
• Formic Acid
• Phenyl Formate
• Formate Ester
• Indole
• Quinolone
• Oxazine
• Pyrrole
• Nitro compounds

Statement dc:rights

• info:eu-repo/semantics/openAccess

Language dc:language

eng

Identifier

http://dx.doi.org/10.13130/abdellatif-manar-ahmed-fouad_phd2024-01-31
10.13130/abdellatif-manar-ahmed-fouad_phd2024-01-31

OAI identifier oai:identifier

oai:air.unimi.it:2434/1026030