A Copper‐Benzotriazole‐Based Coordination Polymer Catalyzes the Efficient One‐Pot Synthesis of (N′‐Substituted)‐hydrazo‐4‐aryl‐1,4‐dihydropyridines from Azines

作者: Michael Kallitsakis , Edward Loukopoulos , Alaa Abdul-Sada , Graham J. Tizzard , Simon J. Coles

DOI: 10.1002/ADSC.201601072

关键词:

摘要: A series of new (N’-substituted)-hydrazo-4-aryl-1,4 dihydropyridines were successfully synthesized via a facile one pot catalytic pathway utilizing azines and propiolate esters as starting materials 1D Cu benzotriazoles based coordination polymer catalyst. In the absence catalyst, corresponding 5-substituted 4,5-dihydro pyrazoles formed in moderate to high yields. Fine-tuning catalysts allowed us gain more insights regarding plausible reaction mechanism.

参考文章(39)
Shunsuke Sueki, Ryo Takei, Yuto Zaitsu, Junya Abe, Akane Fukuda, Keisuke Seto, Yukio Furukawa, Isao Shimizu, Synthesis of 1,4-dihydropyridines and their fluorescence properties European Journal of Organic Chemistry. ,vol. 2014, pp. 5281- 5301 ,(2014) , 10.1002/EJOC.201402426
Nagarjun Narayanaswamy, T. Govindaraju, Aldazine-based colorimetric sensors for Cu2+ and Fe3+ Sensors and Actuators B-chemical. ,vol. 161, pp. 304- 310 ,(2012) , 10.1016/J.SNB.2011.10.036
Fahmi Himo, Timothy Lovell, Robert Hilgraf, Vsevolod V. Rostovtsev, Louis Noodleman, K. Barry Sharpless, Valery V. Fokin, Copper(I)-Catalyzed Synthesis of Azoles. DFT Study Predicts Unprecedented Reactivity and Intermediates Journal of the American Chemical Society. ,vol. 127, pp. 210- 216 ,(2005) , 10.1021/JA0471525
Wei Lee Leong, Jagadese J. Vittal, One-Dimensional Coordination Polymers: Complexity and Diversity in Structures, Properties, and Applications Chemical Reviews. ,vol. 111, pp. 688- 764 ,(2011) , 10.1021/CR100160E
P. Ricardo Girling, Andrei S. Batsanov, Hong C. Shen, Andrew Whiting, A multicomponent formal [1+2+1+2]-cycloaddition for the synthesis of dihydropyridines Chemical Communications. ,vol. 48, pp. 4893- 4895 ,(2012) , 10.1039/C2CC31495A
Wafa Gati, Mohamed M. Rammah, Mohamed B. Rammah, François Couty, Gwilherm Evano, De Novo Synthesis of 1,4-Dihydropyridines and Pyridines Journal of the American Chemical Society. ,vol. 134, pp. 9078- 9081 ,(2012) , 10.1021/JA303002A
Satyanarayana Battula, Ram A. Vishwakarma, Qazi Naveed Ahmed, Cu–benzotriazole-catalyzed electrophilic cyclization of N-arylimines: a methodical tandem approach to O-protected-4hydroxyquinazolines- RSC Advances. ,vol. 4, pp. 38375- 38378 ,(2014) , 10.1039/C4RA07377K
Jiri Verner, Milan Potacek, Criss-cross cycloadditions on ketazines derived from alicyclic ketones. Molecules. ,vol. 11, pp. 34- 42 ,(2006) , 10.3390/11010034