136269-09-5Relevant academic research and scientific papers
Isomerization and ring-closing metathesis for the synthesis of 6-, 7- and 8-membered benzo- and pyrido-fused N,N-, N,O- and N,S-heterocycles
Van Otterlo, Willem A.L.,Morgans, Garreth L.,Khanye, Setshaba D.,Aderibigbe, Blessing A.A.,Michael, Joseph P.,Billing, David G.
, p. 9171 - 9175 (2004)
An isomerization-ring-closing metathesis (RCM) strategy afforded N-substituted 4H-1,4-benzoxazines from the protected N-allyl-2-(allyloxy) anilines. In addition, RCM was used to synthesize the N-substituted, 8-membered benzo-fused heterocycles from the re
A ring-closing metathesis approach to eight-membered benzannelated scaffolds and subsequent internal alkene isomerizations
Taher, Abu,Aderibigbe, Blessing A.,Morgans, Garreth L.,Madeley, Lee G.,Khanye, Setshaba D.,Van Der Westhuizen, Leandi,Fernandes, Manuel A.,Smith, Vincent J.,Michael, Joseph P.,Green, Ivan R.,Van Otterlo, Willem A.L.
, p. 2038 - 2047 (2013/03/13)
A set of eight-membered benzannelated heterocycles containing two heteroatoms (O,O, NR,NR and O,NR where R=protecting group) was synthesized by ring-closing metathesis from the corresponding ortho-bis-allyl precursors. In this manner, 7-methoxy-2,5-dihydro-1,6-benzodioxocine, 1,2,5,6-tetrahydro-1,6- benzodiazocines, 5,6-dihydro-2H-1,6-benzoxazocines and 5,6,9,10- tetrahydropyrido[2,3-b][1,4]diazocine were synthesized. A number of these compounds were then treated with the catalyst [RuClH(CO)(PPh3) 3] to facilitate isomerization of the alkene into conjugation with the heteroatoms in the eight-membered ring. Quite surprisingly, an equal ratio of regioisomers was obtained, even if the heteroatoms were different.
