THEORETICAL INVESTIGATION OF THE REACTION OF UNSYMMETRICAL 3,6-DISUBSTITUTED <i>sym</i>-TETRAZINES WITH CERTAIN ENAMINES

Authors

  • Е. С. Афонькина Chelyabinsk State University, Chelyabinsk 454021
  • В. А. Потемкин Chelyabinsk State Medical Academy, Chelyabinsk 454092
  • М. А. Гришина Chelyabinsk State Medical Academy, Chelyabinsk 454092

DOI:

https://doi.org/10.1007/4920

Keywords:

sym-tetrazine, quantum-chemical semiempirical PM3 method, molecular orbitals, Carboni-Lindsey reaction, HOMO, LUMO, stereoisomer

Abstract

A theoretical investigation has been carried out of the reaction of 6-(3,5-dimethylpyrazol-1-yl)-sym-tetrazin-3-ylhydrazones of ketones with enamines such as 1-morpholinocyclopentene and 1-piperidino-cyclopentene. A [4+2] cycloaddition mechanism of unsymmetrical 3,6-disubstituted tetrazines with enamines is proposed (the Carboni–Lindsey reaction). As a result only one product is preferentially obtained, having a substituent in the ortho position relative to the dimethylpyrazolyl radical, however in the case of small steric problems under kinetic conditions, control of the process is possible and all possible stereoisomers are obtained.

How to Cite

Afonkina, E. S.; Potemkin, V. A.; Grishina, M. A. Chem. Heterocycl. Compd. 2010, 46, 983. [Khim. Geterotsikl. Soedin. 2010, 1217.]

For this article in the English edition see DOI 10.1007/s10593-010-0611-1

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Published

2019-01-16

Issue

No. 8 (2010)

Section

Original Papers