23263-96-9Relevant articles and documents
REACTIONS OF SODIUM SALTS OF TOSYLHYDRAZONE COMPOUNDS WITH SILVER CHROMATE. FORMATION OF INDAZOLE, PYRAZOLE, AND BENZONITRILE DERIVATIVES.
Saito,Toda,Mukai
, p. 1567 - 1569 (1984)
Tropone tosylhydrazone sodium salt was allowed to react with silver chromate to give 2-tosyl-2H-indazole. The reaction is thought to proceed through the cyclization of the hydrazyl radical intermediate. Under the same conditions, sodium salts of m-nitrobenzaldehyde tosylhydrazone (5), benzylideneacetone tosylhydrazone derivatives (7a and 7b), and beta -ionone tosylhydrazone (9) reacted to yield m-nitrobenzonitrile from 5 and pyrazole derivatives from 7a, b, and 9, respectively. m-Nitrobenzonitrile is formed by homolytic fission of nitrogen-nitrogen bond of 5. Formation of the pyrazole derivatives can be explained by intramolecular 1,3-dipolar additions of the corresponding diazo intermediates.
Predicting the catalytic activity of azolium-based halogen bond donors: an experimentally-verified theoretical study
Bolotin, Dmitrii S.,Il'in, Mikhail V.,Novikov, Alexander S.,Suslonov, Vitalii V.,Sysoeva, Alexandra A.
, p. 7611 - 7620 (2021/09/22)
This report demonstrates the successful application of electrostatic surface potential distribution analysis for evaluating the relative catalytic activity of a series of azolium-based halogen bond donors. A strong correlation (R2> 0.97) was observed between the positive electrostatic potential of the σ-hole on the halogen atom and the Gibbs free energy of activation of the model reactions (i.e., halogen abstraction and carbonyl activation). The predictive ability of the applied approach was confirmed experimentally. It was also determined that the catalytic activity of azolium-based halogen bond donors was generally governed by the structure of the azolium cycle, whereas the substituents on the heterocycle had a limited impact on the activity. Ultimately, this study highlighted four of the most promising azolium halogen bond donors, which are expected to exhibit high catalytic activity.
Monohydrochloride Assisted Synthesis of Functionalized Isoxazoles and Pyrazoles from Allenic Ketones: First Synthesis of (Z)-2-Methyl-7H-benzo[b]pyrazolo[5,1-d][1,5]oxazocines
Sarkar, Debayan,Sahoo, Sushree Ranjan
, p. 2035 - 2049 (2019/03/07)
A facile hydrochloride promoted regioselective synthesis of isoxazoles and pyrazoles from 1,2-allenic ketones is reported. The reaction has been scaled up to gram scale. A direct 8-endo dig ring annulations towards the first synthesis of (Z)-2-methyl-7H-b