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NOVEL APPROACH FOR THE SYNTHESIS OF N-UNSUBSTITUTED 2,3,5,6-TETRAHYDRO-4H-2,6-METHANO-1,3-BENZOXAZOCINE-4-THIONES

Alexander V. Borisov, Svitlana S. Kovalenko, Sergiy M. Kovalenko
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Abstract


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.

How to Cite
Borisov, A. V.; Kovalenko, S. S.; Kovalenko, S. M. Chem. Heterocycl. Compd. 2015, 51, 678. [Khim. Geterotsikl. Soedin. 2015, 51, 678.]

For this article in the English edition see DOI 10.1007/s10593-015-1756-8


Keywords


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

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