23102-13-8Relevant academic research and scientific papers
Microwave-assisted rapid and simplified hydrogenation
Banik, Bimal K.,Barakat, Khaled J.,Wagle, Dilip R.,Manhas, Maghar S.,Bose, Ajay K.
, p. 5746 - 5753 (2007/10/03)
Catalytic transfer hydrogenation has been conducted under microwave irradiation in open vessels using high-boiling solvents such as ethylene glycol (bp 198 °C) as the microwave energy transfer agent. Reduction of double bonds and hydrogenolysis of several functional groups were carried out safely and rapidly (3-5 min) at about 110-130 °C with 10% Pd/C as an efficient catalyst and ammonium formate as the hydrogen donor. Diverse types of β-lactam synthons were prepared by the reduction of ring substituents containing alkene and alkylidene groups or conjugated unsaturated esters. Cleavage of the β-lactam ring by hydrogenolysis of the N-C4 bond of 4- aryl-2-azetidinones was a facile reaction with 10% Pd/C as the catalyst; but no ring scission occurred when Raney nickel catalyst was employed. Dehalogenation of aromatic compounds was also successful with ammonium formate and Pd/C catalyst. Hydrogenolysis of phenylhydrazone of methyl benzoylformate gave the methyl ester of phenylglycine in excellent yield. The techniques described here for microwave assisted hydrogenation are safe, rapid, and efficient and are suitable for research investigation as well as for undergraduate and high school laboratory exercises.
Thermally Induced Fragmentation and Cyclisation of C-Azidohydrazones
Bruche, Luca,Garanti, Luisa,Zecchi, Gaetano
, p. 619 - 624 (2007/10/02)
C-Azidohydrazones 2 were synthesized from the corresponding C-chlorohydrazones 1 and submitted to thermal decomposition in boiling benzene.Various kinds of products were obtained due to competitive modes of evolution of first-formed nitrenes 13, namely hydrogen abstraction to form aminohydrazones 3 and benzotriazepine 8, and radical fragmentation to give ultimatively diaryls 4 and arylglyoxylate arylhydrazones 5.Ring-closed products, namely 1,2,4-triazoles 6 and imidazolones 7 were also formed.
