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Tetrazole and triazole

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Tetrazoles and triazole synthesis and applications

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Tetrazole and triazole

  1. 1. Shrikant G. Pharande Tetrazoles and Triazoles Synthesis and applications
  2. 2. 1, 5 di-substituted tetrazole 5 -substituted tetrazole Tetrazoles
  3. 3. 1.Introduction - five-membered, doubly unsaturated ring consisting of one carbon and four nitrogen atoms
  4. 4. 1.Introduction - five-membered, doubly unsaturated ring consisting of one carbon and four nitrogen atoms - they are unknown to nature
  5. 5. 1.Introduction - five-membered, doubly unsaturated ring consisting of one carbon and four nitrogen atoms - they are unknown to nature - divided in three types parent monosubstituted disubstituted
  6. 6. 1.Introduction - five-membered, doubly unsaturated ring consisting of one carbon and four nitrogen atoms - they are unknown to nature - divided in three types - exist in the tautomeric forms Mol Divers. 2015,19(1):189-212
  7. 7. 1.Introduction - tetrazoles are stable to various chemical reagents such as oxidants, acids, bases, alkylating agents, dienophiles, etc.
  8. 8. 1.Introduction - tetrazoles are stable to various chemical reagents such as oxidants, acids, bases, alkylating agents, dienophiles, etc. - thermal stability is high
  9. 9. 1.Introduction - tetrazoles are stable to various chemical reagents such as oxidants, acids, bases, alkylating agents, dienophiles, etc. - thermal stability is high - tetrazoles are medicinally important Mol Divers. 2015,19(1):189-212
  10. 10. Chemical Reviews ,41,1,1947 First synthesized tetrazole by J. A. Bladin in 1885 2. Synthesis
  11. 11. 2. Synthesis Unsubstituted tetrazole Z. Anorg. Allg. Chem. 2008, 17111723
  12. 12. 2. Synthesis R = alkyl or aryl Eur. J. Org. Chem., 2012, 31, 6101. 5- sub. tetrazoles
  13. 13. 2. Synthesis 5- sub. tetrazoles by deprotection
  14. 14. 2. Synthesis 1, 5- sub. tetrazoles By using Ugi-azide Tetrahedron 67 (2011) 8902-8909 J. Mex. Chem. Soc. 2013, 57(4)
  15. 15. 2. Synthesis One pot ugi-azide reaction J. Mex. Chem. Soc. 2013, 57(4)
  16. 16. Ugi-azide reaction mechanism J. Mex. Chem. Soc. 2013, 57(4)
  17. 17. Ugi-azide reaction literature survey Org. Biomol. Chem., 2013, 11, 6036. 29-66% 8 examples
  18. 18. One pot ugi-azide/cyclisation EUR. J. ORG. CHEM.,16, 2014, 3379–
  19. 19. Enantioselective Passerini-Type Reaction Angew. Chem. Int. Ed. 2008, 47, 9454 –9457
  20. 20. Enantioselective isoquinoline-tetrazole by ugi-azide
  21. 21. 3. Reactivity 5- sub. Tetrazoles - alkylation Eur. J. Org. Chem., 2012, 31, 6101.
  22. 22. 3. Reactivity 5- sub. Tetrazoles - arylation Eur. J. Org. Chem., 2012, 31, 6101.
  23. 23. 4. Applications Medicinal chemistry Chemistry of Heterocyclic Compounds, Vol. 43, No. 1, 2007
  24. 24. 4. Applications Medicinal chemistry Chemistry of Heterocyclic Compounds, Vol. 43, No. 1, 2007
  25. 25. 4. Applications agrochemistry J. Agric. Food Chem. 1989, 37, 196-200 J. Agric. Food Chem. 2004, 52, 8081-8085
  26. 26. 4. Applications Other applications – in fluorescent Inorganica Chimica Acta 432 (2015) 50 Dalton Trans., 2014, 43, 6429–6435
  27. 27. 4. Applications Other applications - components of various combustible and thermally decomposing systems including solid propellants, blowing agents and initiating explosives. -selective recovering of palladium from the industrial wastes
  28. 28. 1,2,3 triazoles
  29. 29. 1.Introduction five-membered ring of two carbon atoms and three nitrogen atoms Divided in three main groups Monocyclic 1,2,3 triazole benzotriazole 1,2,3 triazolium salt
  30. 30. 1.Introduction Medicinal chemistry Agrochemicals Fluorescent materials dyes Polymer chemistry Chem. Rev. 2008, 108, 2952–3015
  31. 31. 2. Synthesis 1. Without using catalyst 2. By using catalyst Chem. Rev. 2008, 108, 2952–3015
  32. 32. 2. Synthesis HR' H+ CuLxR' N N N R2 CuLxR' N N N R2 CuLx N N N R1 R2 N N N R CuLx H+ N N N R H R2 R2 [CuLx] RDS J. Am. Chem. Soc, 2005, 127, 210-216. Organometallics 2007, 26, 4389-4391. Mechanism
  33. 33. 2. Synthesis Ugi- triazoles – linked triazole 99-100% 20 examples Bioorg. Med. Chem. Lett. 22 (2012) 2598–2603 R2 = n-butyl, 2-F, 4- Cl, Bn R1 = 2-Br, 2-Cl, 2-F, 4-F
  34. 34. 2. Synthesis Ugi- triazoles – 6 component ugi ACS Comb. Sci. 2014, 16, 176−183 17 examples 81-92%
  35. 35. 2. Synthesis Ugi- triazoles – peptoid mimics Org. Biomol. Chem., 2011, 9, 5024–5027
  36. 36. 2. Synthesis Ugi- triazoles – fused triazole Tetrahedron Lett. 2004, 45, 8439 86-98%7 examples
  37. 37. 2. Synthesis Ugi- triazoles – fused triazole 39-94%13 examples Org. Biomol. Chem., 2014, 12, 6986–6989
  38. 38. 2. Synthesis Ugi- triazoles – macrocycles in pot Oxazole intermediate Org. Lett., 2006, 8, 4145
  39. 39. 2. Synthesis Ugi- triazoles – click and post condensation Eur. J. Org. Chem.,2013, 1223 One example by using terminal alkyne
  40. 40. 3. Reactivity Alkyl nucleophilic sub. reaction 1:1.7 Farmaco 60 (2005) 367–375 Pd catalysed arylation at c5 Org. Lett., 9, 2007, 2333
  41. 41. 4. Applications Medicinal chemistry Chem. Asian J. 2011, 6, 2696 – 2718
  42. 42. 4. Applications I Agrochemistry Org. Biomol. Chem., 2015, 13, 477–486 PCT Int. Appl. (2013), WO 2013037289 A1 J. Agric. Food Chem. 2006, 54, 1361-1372
  43. 43. 4. Applications Fluorescent compounds Org. Biomol. Chem., 2014, 12, 5158 Synthesis 2014, 46, 3239–3248 Organogelator and fluorescent Tetrahedron 71 (2015) 2124. fluoroionophores Chem. Commun., 2014, 50, 14167 Antimicrobial and fluorescent Eur. J. Med. Chem. 77 ,2014,145.

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