NUCLEOPHILIC SUBSTITUTION IN 1-ALKYL-4,5-DICHLORO-3-NITROPYRIDAZIN-6-ONES

Authors

  • Ю. М. Воловенко Taras Shevchenko National University, Kiev 01033
  • Т. А. Воловненко Taras Shevchenko National University, Kiev 01033

DOI:

https://doi.org/10.1007/8005

Keywords:

2-azahetarylacetonitriles, 1-alkyl-4, 5-dichloro-3-nitropyridazin-6-ones, ambident nucleophiles, 6, 7-dihydro-1H-pyrrolo[2, 3-d]pyridazin-7-ones, malonodinitrile, CH-acids, C-nucleophiles, nucleophilic substitution

Abstract

Treatment of 1-alkyl-4,5-dichloro-3-nitropyridazin-6-one with C-nucleophiles and with ambident nucleophiles (2-azahetarylacetonitriles) leads to a selective substitution of a chorine atom by the quaternary carbon atom of the carbanion formed from a substituted acetonitrile. The pKa of the CH-acid 2-(1-alkyl-5-chloro-3-nitro-6-oxo-1,6-dihydro-4-pyridazinyl)malononitrile was determined by potentiometric titration. Reaction of 2-(1-alkyl-5-chloro-3-nitro-6-oxo-1,6-dihydro-4-pyridazinyl)-2-hetarylacetonitriles with primary amines gives 6,7-dihydro-1H-pyrrolo[2,3-d]pyridazin-7-ones.

How to Cite
Volovenko, Yu. M.; Volovnenko, T. A.  Chem. Heterocycl. Compd. 2006, 42, 488. [Khim. Geterotsikl. Soedin. 2006, 556.]

For this article in the English edition, see DOI 10.1007/s10593-006-0115-1

 

Downloads

Published

2023-08-30

Issue

No. 4 (2006)

Section

Original Papers