Heterocycles p. 1519 - 1526 (2001)
Update date:2022-09-26
Topics:
Lee, Jae Yeol
Baek, Nam Jun
Lee, Sook Ja
Park, Hokoon
Lee, Yong Sup
Tetracyclic dibenzo[c,f]-4-oxopyrrolo[1,2-c]azepine (2a), dibenzo[c,f]-5-oxopiperido[1,2-c]azepine (2b), benzo[f]-4-oxopyrrolo[1,2-a]thieno[3,2-c]azepine (2c), and benzo[f]-5-oxopiperido[1,2-a]thieno[3,2-c]azepine (2d) were prepared through intramolecular N-acyliminium ion cyclization of hydroxylactams (3a-d) with aromatic or heteroaromatic rings such as benzene and thiophene as a π-nucleophile. In the case of furan ring, the hydroxylactams (3e, f) were completely decomposed under the acidic conditions (formic acid or methanesulfonic acid). Subsequent reduction of 2a-d with BF3·O(C2H5)2 and BH3·S(CH3)2 finally provided the tetracyclic dibenzo[c,f]pyrrolo[1,2-c]azepine (1a), dibenzo[c,f]piperido[1,2-c]azepine (1b), benzo[f]pyrrolo[1,2-a]thieno[3,2-c]azepine (1c), and benzo[f]piperido[1,2-a]thieno[3,2-c]azepine derivatives (1d) as analogues of mianserin.
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Doi:10.1021/jm010948j
(2001)Doi:10.1016/S0022-328X(01)01006-3
(2001)Doi:10.1002/chem.201204373
(2013)Doi:10.1007/BF00854578
()Doi:10.1016/S0040-4020(01)00759-1
(2001)Doi:10.1039/c29690001313
(1969)