Hydroxylation of 5 H ‐3‐Oxo‐2,3,6,7,8,9‐hexahydroimidazo[1,2‐ a ]azepine derivatives by molecular oxygen | Zendy

Campagna Francesco | Zendy; Carotti Angelo | Zendy; Casini Giovanni | Zendy

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Hydroxylation of 5 H ‐3‐Oxo‐2,3,6,7,8,9‐hexahydroimidazo[1,2‐ a ]azepine derivatives by molecular oxygen

Author(s) -

Campagna Francesco,

Carotti Angelo,

Casini Giovanni

Publication year - 1990

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570270723

Subject(s) - chemistry , azepine , hydroxylation , isomerization , stereochemistry , oxygen , oxygen atom , medicinal chemistry , organic chemistry , molecule , catalysis , enzyme

O ‐Methylcaprolactim 3 reacts in hot dimethylsulfoxide with α‐amino acids 4 to give 5 H ‐3‐oxo‐2,3,6,7,8,9‐hexahydroimidazo[1,2‐ a ]azepines 6 and, unexpectedly, hydroxylated derivatives 7a,c and 8c . The structures of the hydroxylated compounds have been elucidated by spectroscopic means and, when necessary, further confirmed by an independent unequivocal synthesis. The formation of 7 as well as the isomerization of 7c to 8c are discussed in detail.

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