Synthèse et réactivité des dérivés de la 2,3-dihydro-3-hydroxy-2-phényl-1,5-benzothiazépin-4(5H)-one

Zerzouf, Abdelfettah; Meslouhi, H. El; Salem, Mohamed A.; Essassi, El Mokhtar; Roumestant, M. L.; Viallefont, Ph.

doi:10.1016/s1387-1609(01)01301-9

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2023

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“…The first description of such a reaction was demonstrated by the contraction of the tropolone ring of colchicine to benzene, known as the colchicine-allocolchicine rearrangement . Later, it was discovered that other cycloheptatrienes, oxepines, 1,4-oxazepines, 3H-1-benzazepines, − 1,4-benzodiazepines, and 1,4- and 1,5-benzothiazepines also undergo similar transformations. Despite this rearrangement, with aromatization being characteristic of various types of unsaturated seven-membered rings, it remains poorly understood.…”

Section: Introductionmentioning

confidence: 99%

Photoinitiated Rearrangement of Aromatic Azides to 2-Aminonicotinates

Davydov,

Giricheva,

Malysheva

et al. 2023

J. Org. Chem.

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This study describes a one-pot photoinduced method for azepine synthesis and their subsequent rearrangement into pyridines. The rearrangement of the azepine, formed during photolysis, occurs due to both thermal and photochemical activation of the reaction. This requires an electron-donating substituent at the second position of the azepine and an electron-withdrawing substituent at the third position of the azepine. A reaction mechanism has been proposed to explain the role of water and the nature of the azepine substituents.

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