A New Synthesis of 5-Phenyl-2,3-dihydro- and 2,3,4,5-Tetrahydro-1H-2-benzazepin-1-ones

Autor:	J. M. Muchowski, K. Ackerman, D. E. Horning
Rok vydání:	1972
Předmět:	chemistry.chemical_classification Chemistry Organic Chemistry Sulfuric acid General Chemistry medicine.disease Catalysis Benzazepine Phthalide chemistry.chemical_compound medicine Organic chemistry Dehydration Lactone
Zdroj:	Canadian Journal of Chemistry. 50:3886-3891
ISSN:	1480-3291 0008-4042
DOI:	10.1139/v72-612
Popis:	It was shown that 3-phenyl-3-(2-aminoethyl)phthalide (6, R = H) and its N-methyl analog (6, R = CH3) existed in the amino lactone form in solution at room temperature. In the absence of solvents, however, these compounds underwent a spontaneous transformation into the 5-phenyl-2,3,4,5-tetrahydro-1H-2-benzazepin-1-ones (8, R = H, CH3) which suffered dehydration in sulfuric acid with the formation of 5-phenyl-2,3-dihydro-1H-2-benzazepin-1-ones (9, R = H, CH3).This benzazepine synthesis can be considered to be analogous to the known (12–15) conversion of 1-aminomethylphthalides (11) to 4-hydroxy-3,4-dihydroisocarbostyrils (13).
Databáze:	OpenAIRE
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