Nucleophilic Addition of Amines to Ruthenium Carbenes:  ortho ‐(Alkynyloxy)benzylamine Cyclizations towards 1,3‐Benzoxazines | Zendy

GonzálezRodríguez Carlos | Zendy; Suárez José Ramón | Zendy; Varela Jesús A. | Zendy; Saá Carlos | Zendy

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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.

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