Premium
One‐Pot Procedure for the Synthesis of 1,5‐Benzodiazepines from N ‐Allyl‐2‐bromoanilines
Author(s) -
Weers Marco,
Lühning Lars H.,
Lührs Vanessa,
Brahms Christian,
Doye Sven
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201604561
Subject(s) - chemistry
A new one‐pot procedure that includes an initial titanium‐catalyzed intermolecular hydroaminoalkylation of N ‐allyl‐2‐bromoanilines with N ‐methylanilines and a subsequent intramolecular Buchwald–Hartwig amination directly gives access to pharmacologically relevant 1,5‐benzodiazepines. The process takes advantage of the excellent regioselectivity of the initial hydroaminoalkylation performed in the presence of a titanium mono(formamidinate) catalyst and the fact that the exclusively formed branched hydroaminoalkylation products can only undergo palladium‐catalyzed cyclization to 1,5‐benzodiazepines.