A ring-closing metathesis approach to eight-membered benzannelated scaffolds and subsequent internal alkene isomerizations

作者：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^*

来源：Tetrahedron, 2013, 69(8): 2038-2047.

DOI：10.1016/j.tet.2012.12.043

• Ring-closing metathesis
• Isomerization
• Benzodioxocine
• Benzodiazocine
• Benzoxazocine
• Pyridodiazocine

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 orthobis-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.

• 出版日期2013-2-25