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Nucleophilic Addition of Amines to Ruthenium Carbenes: ortho ‐(Alkynyloxy)benzylamine Cyclizations towards 1,3‐Benzoxazines
Author(s) -
GonzálezRodríguez Carlos,
Suárez José Ramón,
Varela Jesús A.,
Saá Carlos
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201410284
Subject(s) - ruthenium , benzylamine , carbene , chemistry , nucleophile , medicinal chemistry , catalysis , organic chemistry , combinatorial chemistry
A new ruthenium‐catalyzed cyclization of ortho ‐(alkynyloxy)benzylamines to dihydro‐1,3‐benzoxazines is reported. The cyclization is thought to take place via the vinyl ruthenium carbene intermediates which are easily formed from [Cp*RuCl(cod)] and N 2 CHSiMe 3 . The mild reaction conditions and the efficiency of the procedure allow the easy preparation of a broad range of new 2‐vinyl‐2‐substituted 1,3‐benzoxazine derivatives. Rearrangement of an internal C(sp) in the starting material into a tetrasubstituted C(sp 3 ) atom in the final 1,3‐benzoxazine is highly remarkable.