Synthesis of Medium-Ring-Sized Benzolactams by Using Strong Electrophiles and Quantitative Evaluation of Ring-Size Dependency of the Cyclization Reaction Rate

Autor:	Tomohiko Ohwada, Hiroaki Kurouchi
Rok vydání:	2019
Předmět:	Order of reaction 010405 organic chemistry Chemistry Organic Chemistry Electrophilic aromatic substitution 010402 general chemistry Ring (chemistry) 01 natural sciences Medicinal chemistry 0104 chemical sciences Dilution Ring size Reaction rate Electrophile
Zdroj:	The Journal of organic chemistry. 85(2)
ISSN:	1520-6904
Popis:	Benzolactams with medium-sized rings were synthesized via the electrophilic aromatic substitution reaction of carbamoyl cations (R1R2N+═C═O) in good to high yields without dilution. These reactions were utilized to quantitatively examine the extent of retardation of medium-sized ring formation, compared to five- or six-membered ring formation. The order of reaction rates of formation of cyclic benzolactams is six- > five- > seven- > eight- > nine-membered ring at 25 °C. The present reaction provides a route to eight- and nine-membered benzolactams.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::1997a24173bb1694f652889cc4568da3 https://pubmed.ncbi.nlm.nih.gov/31800245 Zobrazit plný text záznamu