Novel approach for the synthesis of N-unsubstituted 2,3,5,6-tetrahydro-4H-2,6-methano-1,3-benzoxazocine-4-thiones

作者：Borisov Alexander V^*; Kovalenko Svitlana S; Kovalenko Sergiy M

来源：Chemistry of Heterocyclic Compounds, 2015, 51(7): 678-681.

DOI：10.1007/s10593-015-1756-8

• lortalamine
• 2,6-methano-1,3-benzoxazocine-4-thiones
• 6-methano-1,3-benzoxazocin-4-one
• pyridoxal
• tandem reaction

An efficient one-pot method for the synthesis of 2,3,5,6-tetrahydro-4H-2,6-methano-1,3-benzoxazocine-4-thiones in high yields has been developed via regioselective tandem reaction of coumarin-3-thioamides and ketones containing different methylene groups. Further oxidation with hydrogen peroxide under basic conditions leads to the formation of N-unsubstituted derivatives of 2,3,5,6-tetrahydro-4H-2,6-methano-1,3-benzoxazocin-4-one.

• 出版日期2015-7