Abstract
4-Benzotriazolylmethyl-2,3,4,5-tetrahydro-1,4-benzothiazepines
5a,b
, -1,4-benzoxazepine (
12
) and -1,4-benzodiazepine (
20
) are obtained
via
aluminium chloride mediated intramolecular cyclizations of
N
,
N
-bis(1
H
-1,2,3-benzotriazol-1-ylmethyl)-2-(arylthio)ethan-1-amines
4a,b
, -2-(phenoxy)ethan-1-amine (
11
) and -
N
-[2-(
N
′-methylanilino)ethyl]amine (
19
), respectively. Subsequent nucleophilic substitutions of the benzotriazolyl group in
5a,b
,
12
and
20
succeeded with Grignard reagents, triethyl phosphite, sodium borohydride, and a silyl enol ether to give novel 2,3,4,5-tetrahydro-1,4-benzothiazepines
6-9
, -1,4-benzoxazepines
13
and
14
, and -1,4-benzodiazepines
21-23
in good yields.