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Home » flow synthesis » Multistep Flow Synthesis of 5-Amino-2-aryl-2H-[1,2,3]-triazole-4- carbonitrilesultistep Flow Synthesis of 5-Amino-2-aryl-2H-[1,2,3]-triazole-4- carbonitriles

Multistep Flow Synthesis of 5-Amino-2-aryl-2H-[1,2,3]-triazole-4- carbonitrilesultistep Flow Synthesis of 5-Amino-2-aryl-2H-[1,2,3]-triazole-4- carbonitriles

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Using the Uniqsis FlowSyn flow chemistry system researchers from the UCB Biopharma. Belgium have developed a flow synthesis of 2-substituted 1,2,3-triazoles that demonstrates improvements over the conventional batch route.

The route involves the diazotisation of anilines and condensation with malononitrile followed by the nucleophilic addition of ammonia or an alkylamine and finally a novel copper catalysed cyclisation. The intermediate azide was generated and consumed in situ which enabled safe scale up under the flow-through conditions employed.

DOI: 10.1002/chem.201402074

Multistep Flow Synthesis of 5-Amino-2-aryl-2H-[1,2,3]-triazole-4-carbonitriles

Authors, Dr. Jérôme Jacq, Dr. Patrick Pasau

Corresponding author

  1. UCB Biopharma, Avenue de l’Industrie, 1420 Braine l’Alleud (Belgium)
  • UCB Biopharma, Avenue de l’Industrie, 1420 Braine l’Alleud (Belgium)===

1,2,3-Triazole has become one of the most important heterocycles in contemporary medicinal chemistry. The development of the copper-catalyzed Huisgen cycloaddition has allowed the efficient synthesis of 1-substituted 1,2,3-triazoles. However, only a few methods are available for the selective preparation of 2-substituted 1,2,3-triazole isomers. In this context, we decided to develop an efficient flow synthesis for the preparation of various 2-aryl-1,2,3-triazoles. Our strategy involves a three-step synthesis under continuous-flow conditions that starts from the diazotization of anilines and subsequent reaction with malononitrile, followed by nucleophilic addition of amines, and finally employs a catalytic copper(II) cyclization. Potential safety hazards associated with the formation of reactive diazonium species have been addressed by inline quenching. The use of flow equipment allows reliable scale up processes with precise control of the reaction conditions. Synthesis of 2-substituted 1,2,3-triazoles has been achieved in good yields with excellent selectivities, thus providing a wide range of 1,2,3-triazoles.http://onlinelibrary.wiley.com/wol1/doi/10.1002/chem.201402074/full

http://onlinelibrary.wiley.com/store/10.1002/chem.201402074/asset/supinfo/chem_201402074_sm_miscellaneous_information.pdf?v=1&s=77c885224607254b0d594d6cd190e655dd4ac7ee

NMR2002

1H/13c NMR OF 1a

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NMR1001

 

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UCB Biopharma,  Belgium

 

 

 

Uniqsis FlowSyn

 

Uniqsis Ltd
29 Station Road
Shepreth
Cambridgeshire
SG8 6GB
UK
Telephone
+44 (0)845 864 7747
Email
info@uniqsis.com

 

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DR ANTHONY CRASTO

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DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO, Born in Mumbai in 1964 and graduated from Mumbai University, Completed his Ph.D from ICT, 1991,Matunga, Mumbai, India, in Organic Chemistry, The thesis topic was Synthesis of Novel Pyrethroid Analogues, Currently he is working with GLENMARK PHARMACEUTICALS LTD, Research Centre as Principal Scientist, Process Research (bulk actives) at Mahape, Navi Mumbai, India. Total Industry exp 29 plus yrs, Prior to joining Glenmark, he has worked with major multinationals like Hoechst Marion Roussel, now Sanofi, Searle India Ltd, now RPG lifesciences, etc. He has worked with notable scientists like Dr K Nagarajan, Dr Ralph Stapel, Prof S Seshadri etc, He did custom synthesis for major multinationals in his career like BASF, Novartis, Sanofi, etc., He has worked in Discovery, Natural products, Bulk drugs, Generics, Intermediates, Fine chemicals, Neutraceuticals, GMP, Scaleups, etc, he is now helping millions, has 9 million plus hits on Google on all Organic chemistry websites. His friends call him worlddrugtracker. His New Drug Approvals, Green Chemistry International, All about drugs, Eurekamoments, Organic spectroscopy international, etc in organic chemistry are some most read blogs He has hands on experience in initiation and developing novel routes for drug molecules and implementation them on commercial scale over a 29 year tenure till date Aug 2016, Around 30 plus products in his career. He has good knowledge of IPM, GMP, Regulatory aspects, he has several International patents published worldwide . He has good proficiency in Technology transfer, Spectroscopy, Stereochemistry, Synthesis, Polymorphism etc., He suffered a paralytic stroke/ Acute Transverse mylitis in Dec 2007 and is 90 %Paralysed, He is bound to a wheelchair, this seems to have injected feul in him to help chemists all around the world, he is more active than before and is pushing boundaries, He has 9 million plus hits on Google, 2.5 lakh plus connections on all networking sites, 25 Lakh plus views on dozen plus blogs, He makes himself available to all, contact him on +91 9323115463, email amcrasto@gmail.com, Twitter, @amcrasto , He lives and will die for his family, 90% paralysis cannot kill his soul., Notably he has 13 lakh plus views on New Drug Approvals Blog in 212 countries......https://newdrugapprovals.wordpress.com/ , He appreciates the help he gets from one and all, Friends, Family, Glenmark, Readers, Wellwishers, Doctors, Drug authorities, His Contacts, Physiotherapist, etc

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