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

Authors

  • Alexander V. Borisov Enamine Ltd. 23 Alexandra Matrosova St., Kyiv 01103
  • Svitlana S. Kovalenko National University of Pharmacy, 53 Pushkinska St., Kharkiv 61002
  • Sergiy M. Kovalenko V. N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv 61077

DOI:

https://doi.org/10.1007/2547

Keywords:

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

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

Author Biographies

Alexander V. Borisov, Enamine Ltd. 23 Alexandra Matrosova St., Kyiv 01103

Alexander Vladimirovich Borisov

Svitlana S. Kovalenko, National University of Pharmacy, 53 Pushkinska St., Kharkiv 61002

Svitlana Sergievna Kovalenko

Sergiy M. Kovalenko, V. N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv 61077

Sergiy Mikolayovich Kovalenko

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Published

2015-07-31

Issue

Vol. 51 No. 7 (2015)

Section

Original Papers