Molecular orbital calculations for azaquinonoid-ketene and analysis of the intramolecular cycloaddition with the N,N-dimethylanilino group

Autor:	Takachiyo Okuda, Seiji Ito, Masayuki Kuzuya, Fumio Miyake
Rok vydání:	1982
Předmět:	Stereochemistry Chemistry Ketene General Chemistry General Medicine Cycloaddition CNDO/2 Acridone chemistry.chemical_compound Group (periodic table) Intramolecular force Drug Discovery Molecular orbital Derivative (chemistry)
Zdroj:	Chemical and Pharmaceutical Bulletin. 30:1980-1985
ISSN:	1347-5223 0009-2363
DOI:	10.1248/cpb.30.1980
Popis:	Intramolecular cycloaddition of azaquinonoid-ketene (4) generated from benzotriazinone derivative to N, N-dimethylanilino group afforded "unrearranged" acridone in sharp contrast to a carbon analog series (1). Molecular orbital calculations and conformational studies using a model compound did not show much difference between azaquinonoid-ketene (11) and quinonoid-ketene (12), indicating similar propensity toward the [π4a+π2a] pathway of 4 in terms of FMO theory. These results led us to suggest the involvement of a concealed process in the transformation of 4 to "unrearranged" acridone (9), i. e., a [π4a+π2a] cycloaddition at the initial stage, by analogy with the carbon analog (1).
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::98fbefac41a0663462260ccdbcae0470 https://doi.org/10.1248/cpb.30.1980 Zobrazit plný text záznamu