Nucleophilic addition of amines to ruthenium carbenes: Ortho-(alkynyloxy)benzylamine cyclizations towards 1,3-benzoxazines

Angewandte Chemie - International Edition

Volumn 54, Issue 9, 2015, Pages 2724-2728

  González Rodríguez, Carlos ^a   Suárez, José Ramón ^a   Varela, Jesús A ^a   Saá, Carlos ^a  

^a s n   (Spain)

Author keywords

Benzoxazines; Carbenes; Cyclization; Rearrangements; Ruthenium

Indexed keywords

ADDITION REACTIONS; ORGANIC COMPOUNDS; RUTHENIUM; RUTHENIUM COMPOUNDS;

1 ,3-BENZOXAZINE; BENZOXAZINES; CARBENES; CYCLIZATIONS; MILD REACTION CONDITIONS; NUCLEOPHILIC ADDITIONS; REARRANGEMENTS; RUTHENIUM CARBENES;

CYCLIZATION;

EID: 85027954665     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201410284     Document Type: Article

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66. With a poorly coordinating and less nucleophilic nitrogen atom in tosylamide 1o the reaction resulted in a complex mixture. On the other hand, tertiary pyrrolidine derivative 1p was recovered unaltered after 24 h. (Chemical Equation Presented)The reaction of thioether 4 under optimized reaction conditions afforded the corresponding dienyl sulfide 3 in 56% yield and the reaction of tosylamide 5 gave a complex reaction mixture. See Supporting Information for details. (Chemical Equation Presented)The reaction of thioether 4 under optimized reaction conditions afforded the corresponding dienyl sulfide 3 in 56% yield and the reaction of tosylamide 5 gave a complex reaction mixture. See Supporting Information for details. (Chemical Equation Presented)
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