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From 2,5‐Dihydropyrazines to 2 H ‐1,4‐Diazepines and from Benzodihydroarenes to Benzocycloheptene Derivatives, Structural Variants of the Antidepressant Protriptyline
Author(s) -
Schöllkopf Ulrich,
Mittendorf Joachim
Publication year - 1989
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198906131
Subject(s) - ring (chemistry) , chemistry , antidepressant , sigmatropic reaction , stereochemistry , cycloheptatriene , medicinal chemistry , organic chemistry , psychiatry , psychology , anxiety
A hetero‐norcaradiene‐cycloheptatriene rearrangement and an unusually rapid transannular [1,5]‐sigmatropic hydrogen shift are the key steps in the baseinduced ring expansion of the bislactim ethers 1 to the 2 H ‐1,4‐diazepines 2 . The ring expansion is also possible in the case of analogous all‐carbon compounds and leads, for example, from dihydroanthracenes to novel structural variants of the antidepressant protriptyline such as 3 . Examples for R 1 R 3 : H, Me, OMe, Ph, CH 2 Ph.