Safer, greener, and more facile alternatives for synthesis with organic azides

Current Organic Synthesis

Volumn 11, Issue 5, 2014, Pages 732-750

  Sebeika, Meaghan M ^a   Jones, Graham B ^a  

^a NORTHEASTERN UNIVERSITY   (United States)

Author keywords

Azide; Click chemistry; Continuous flow; Diazo transfer; Green chemistry; Microreactor; Triazole

Indexed keywords

EID: 84924156828     PISSN: 15701794     EISSN: None     Source Type: Journal    
DOI: 10.2174/1570179411666140328221938     Document Type: Article

References (96)

1. Jiang, Y.B.; Kuang, C.X. Recent advances in the synthesis of 1- monosubstituted 1,2,3-triazoles. Mini-Rev. Med. Chem. 2013, 13(5), 713- 719.
2. Maddila, S.; Pagadala, R.; Jonnalagadda, S. B. 1,2,4-Triazoles: A review of synthetic approaches and the biological activity. Lett. Org. Chem. 2013, 10(10), 693-714.
3. Kumar, S.S.; Kavitha, H.P. Synthesis and biological applications of triazole derivatives - A review. Mini-Rev. Org. Chem. 2013, 10(1), 40-65.
4. Voitekhovich, S.V.; Ivashkevich, O.A.; Gaponik, P.N. Synthesis, properties, and structure of tetrazoles: Certain achievements and prospects. Russ. J. Organ. Chem. 2013, 49(5), 635-654.
5. Roh, J.; Vavrova, K.; Hrabalek, A. Synthesis and functionalization of 5- substituted tetrazoles. Eur. J. Org. Chem. 2012, (31), 6101-6118.
6. Moderhack, D. Direct routes to 2H-tetrazoles by cyclization and ring transformation. Heterocycles 2013, 87(3), 493-526.
7. Zhao, X.; Zhang, Y.; Wang, J.B. Recent developments in copper-catalyzed reactions of diazo compounds. Chem. Commun. 2012, 48(82), 10162-10173.
8. Li, H.; Zhang, Y.; Wang, J.B. Reaction of diazo compounds with organoboron compounds. Synthesis 2013, 45(22), 3090-3098.
9. da Silva, F.D.; Jordao, A.K.; da Rocha, D.R.; Ferreira, S.B.; Cunha, A.C.; Ferreira, V.F. Recent advances on the synthesis of heterocycles from diazo compounds. Curr. Org. Chem. 2012, 16(2), 224-251.
10. Zhou, C.H.; Wang, Y. Recent researches in triazole compounds as medicinal drugs. Curr. Med. Chem. 2012, 19(2), 239-280.
11. Labadie, G.R.; de la Iglesia, A.; Morbidoni, H. R. Targeting tuberculosis through a small focused library of 1,2,3-triazoles. Mol. Divers. 2011, 15(4), 1017-1024.
12. Peng, X.M.; Cai, G.X.; Zhou, C.H. Recent Developments in azole compounds as antibacterial and antifungal agents. Curr. Top. Med. Chem. 2013, 13(16), 1963-2010.
13. Anastasopoulou, P.; Kythreoti, G.; Cosmidis, T.; Pyrkotis, C.; Nahmias, V.R.; Vourloumis, D. Synthesis of triazole-functionalized 2-DOS analogues and their evaluation as A-site binders. Bioorg. Med. Chem. Lett. 2014, 24(4), 1122-1126.
14. Singh, H.; Sindhu, J.; Khurana, J.M.; Sharma, C.; Aneja, K.R. Syntheses, biological evaluation and photophysical studies of novel 1,2,3-triazole linked azo dyes. RSC Adv. 2014, 4(12), 5915-5926.
15. Sahoo, S.; Veliyath, S.K.; Mahendra Kumar, C. B. Review on substituted 1, 2, 4-triazoles as potent antifungal and antibacterial agents. Int. J. Res. Pharm. Sci. 2012, 3(2), 326-333.
16. Falci, D.R.; Pasqualotto, A.C. Profile of isavuconazole and its potential in the treatment of severe invasive fungal infections. Infect. Drug Resist. 2013, 6, 163-174.
17. Kumar, N.; Shishu, S.; Kapoor, V.R. Facile Syntheses of novel salts of a triazole antifungal agent with enhanced solubility. J. Heterocycl. Chem. 2013, 50(3), 490-495.
18. Sun, N.B.; Fu, J.Q.; Weng, J.Q.; Jin, J.Z.; Tan, C.X.; Liu, X.H. Microwave assisted synthesis, antifungal activity and DFT theoretical study of some novel 1,2,4-triazole derivatives containing the 1,2,3-thiadiazole moiety. Molecules 2013, 18(10), 12725-12739.
19. Chung, D.H.; Kumarapperuma, S.C.; Sun, Y.; Li, Q.; Chu, Y.K.; Arterburn, J.B.; Parker, W.B.; Smith, J.; Spik, K.; Ramanathan, H.N.; Schmaljohn, C.S.; Jonsson, C.B. Synthesis of 1-beta-D-ribofuranosyl-3-ethynyl-[1,2,4]triazole and its in vitro and in vivo efficacy against Hantavirus. Antivir. Res. 2008, 79(1), 19-27.
20. Xiao, S.; Wang, Q.; Si, L.; Shi, Y.; Wang, H.; Yu, F.; Zhang, Y.; Li, Y.; Wang, C.; Zhang, L.; Zhou, D. Synthesis and anti-HCV entry activity studies of β-cyclodextrin-pentacyclic triterpene conjugates. Chem. Med. Chem., 2014, Pages ahead of print.
21. Sirivolu, V.R.; Vernekar, S.K.V.; Ilina, T.; Myshakina, N.S.; Parniak, M.A.; Wang, Z.Q. Clicking 3 '-azidothymidine into novel potent inhibitors of human immunodeficiency virus. J. Med. Chem. 2013, 56(21), 8765-8780.
22. Ferreira, M.D.G.; Pinheiro, L.C.S.; Santos, O.A.; Pecanha, M.D.S.; Sacramento, C.Q.; Machado, V.; Ferreira, V.F.; Souza, T. M.L.; Boechat, N. Design, synthesis, and antiviral activity of new 1H-1,2,3-triazole nucleoside ribavirin analogs. Med. Chem. Res. 2014, 23(3), 1501-1511.
23. Zheng, Y.C.; Duan, Y.C.; Ma, J.L.; Xu, R.M.; Zi, X.; Lv, W.L.; Wang, M.M.; Ye, X.W.; Zhu, S.; Mobley, D.; Zhu, Y.Y.; Wang, J.W.; Li, J.F.; Wang, Z.R.; Zhao, W.; Liu, H.M. Triazole-Dithiocarbamate Based Selective lysine specific demethylase 1 (lsd1) inactivators inhibit gastric cancer cell growth, invasion, and migration. J. Med. Chem. 2013, 56(21), 8543-8560.
24. Lone, S.H.; Bhat, K.A.; Majeed, R.; Hamid, A.; Khuroo, M.A. Click chemistry inspired facile synthesis and bioevaluation of novel triazolyl analogs of Ludartin. Bioorg. Med. Chem. Lett. 2014, 24(4), 1047-1051.
25. Kurumurthy, C.; Veeraswamy, B.; Rao, P.S.; Kumar, G.S.; Reddy, V.L.; Rao, J.V.; Narsaiah, B. Synthesis of novel 1,2,3-triazole tagged pyrazolo 3,4- b pyridine derivatives and their cytotoxic activity. Bioorg. Med. Chem. Lett. 2014, 24(3), 746-749.
26. Pokhodylo, N.; Shyyka, O.; Matiychuk, V. Synthesis and anticancer activity evaluation of new 1,2,3-triazole-4-carboxamide derivatives. Med. Chem. Res. 2014, 23 (5), 2426-2438.
27. Patani, G.A.; LaVoie, E.J. Bioisosterism: A rational approach in drug design. Chem. Rev. 1996, 96(8), 3147-3176.
28. Jiang, B.; Huang, X.; Yao, H.; Jiang, J.; Wu, X.; Jiang, S.; Wang, Q.; Lu, T.; Xu, J. Discovery of potential anti-inflammatory drugs: diaryl-1,2,4-triazoles bearing N-hydroxyurea moiety as dual inhibitors of cyclooxygenase-2 and 5- lipoxygenase. Bioorg. Med. Chem. 2014, 12(13), 2114-2127.
29. Silvestrini, B. Trazodone: from the mental pain to the "dys-stress" hypothesis of depression. Clin. Neuropharmacol.1989, 12(Suppl 1), S4-10.
30. Meuldermans, W.; van Peer, A.; Hendrickx, J.; Woestenborghs, R.; Lauwers, W.; Heykants, J.; Vanden Bussche, G.; van Craeyvelt, H.; van der Aa, P. Alfentanil pharmacokinetics and metabolism in humans. Anesthesiology 1988, 69(4), 527-534.
31. Williams, G.J.; Colby, C.B. Recombinant human interferon-beta suppresses the replication of HIV and acts synergistically with AZT. J. Interferon Res. 1989, 9(6), 709-718.
32. Kiely, D.G.; Cargill, R.I.; Lipworth, B.J. Acute hypoxic pulmonary vasoconstriction in man is attenuated by type I angiotensin II receptor blockade. Cardiovasc. Res. 1995, 30(6), 875-880.
33. Fursch, H. Fentrazamide - opportunities for weed control in seeded rice Lecspro (fentrazamide & propanil 6.75 & 37.5 WP). Pflanzenschutz- Nachrichten Bayer (English Edition) 2001, 54(1), 127-142.
34. Teng, R.L.; Oliver, S.; Hayes, M.A.; Butler, K. Absorption, Distribution, Metabolism, and Excretion of ticagrelor in healthy subjects. Drug Metab. Dispos. 2010, 38(9), 1514-1521.
35. Kolb, H.C.; Finn, M.G.; Sharpless, K.B. Click chemistry: Diverse chemical function from a few good reactions. Angew. Chem. Int. Edit. 2001, 40(11), 2004.
36. Schneider, S.; Gattner, M.J.; Vrabel, M.; Flugel, V.; Lopez-Carrillo, V.; Prill, S.; Carell, T. Structural insights into incorporation of norbornene amino acids for click modification of proteins. Chem. Bio. Chem., 2013, 14(16), 2114-2118.
37. Tolstyka, Z.P.; Richardson, W.; Bat, E.; Stevens, C.J.; Parra, D.P.; Dozier, J.K.; Distefano, M.D.; Dunn, B.; Maynard, H.D. Chemoselective immobilization of proteins by microcontact printing and bio-orthogonal click reactions. Chem. Bio. Chem. 2013, 14(18), 2464-2471.
38. Bateman, L.A.; Zaro, B.W.; Miller, S.M.; Pratt, M. R. An alkyne-aspirin chemical reporter for the detection of aspirin-dependent protein modification in living cells. J. Am. Chem. Soc. 2013, 135(39), 14568-14573.
39. Voelker, A.E.; Viswanathan, R. Synthesis of a suite of bioorthogonal glutathione s-transferase substrates and their enzymatic incorporation for protein immobilization. J. Org. Chem. 2013, 78(19), 9647-9658.
40. Boyere, C.; Broze, G.; Blecker, C.; Jerome, C.; Debuigne, A. Monocatenary, branched, double-headed, and bolaform surface active carbohydrate esters via photochemical thiol-ene/-yne reactions. Carbohydr. Res. 2013, 380, 29- 36.
41. Ichikawa, S.; Ueno, H.; Sunadome, T.; Sato, K.; Matsuda, A. Tris(azidoethyl)amine hydrochloride; a versatile reagent for synthesis of functionalized Dumbbell Oligodeoxynucleotides. Org. Lett. 2013, 15(3), 694-697.
42. Qian, Y.C.; Ren, N.; Huang, X.J.; Chen, C.; Yu, A.G.; Xu, Z.K. Glycosylation of polyphosphazene nanofibrous membrane by click chemistry for protein recognition. Macromol. Chem. Phys. 2013, 214 (16), 1852-1858.
43. Wu, Z.; Nguyen, V.S.; Liu, Z.K.; Wang, Q.A. A Facile "Click Chemistry" approach to novel flavonol glycoconjugates and their cytotoxic activity. Lett. Org. Chem. 2013, 10(9), 674-682.
44. Ilyas, S.; Ilyas, M.; van der Hoorn, R.A.L.; Mathur, S. Selective conjugation of proteins by mining active proteomes through click-functionalized magnetic nanoparticles. ACS Nano 2013, 7(11), 9655-9663.
45. Fuaad, A.; Azmi, F.; Skwarczynski, M.; Toth, I. Peptide conjugation via CuAAC 'Click' chemistry. Molecules 2013, 18(11), 13148-13174.
46. Santner, T.; Hartl, M.; Bister, K.; Micura, R. Efficient access to 3 '-terminal azide-modified RNA for inverse click-labeling patterns. Bioconjugate Chem. 2014, 25(1), 188-195.
47. Kore, A.R.; Charles, I. Click chemistry based functionalizations of nucleoside, nucleotide and nucleic acids. Curr. Org. Chem. 2013, 17(19), 2164-2191.
48. Ding, L.; An, J.; Zhu, Z. A "Click" approach to facile synthesis of long-chain highly branched ROMP polymers. Polym. Chem. 2014, 5(3), 733-742.
49. Bunz, U.H.F. Adventures of an occasional click chemist. Synlett 2013, 24(15), 1899-1909.
50. Lee, D.H.; Kim, K.T.; Jang, Y.; Lee, S.; Jeon, H.B.; Paik, H.J.; Min, B.S.; Kim, W. 1,2,3-triazole crosslinked polymers as binders for solid rocket propellants. J. Appl. Polym. Sci. 2014, Ahead of Print.
51. Thundimadathil, J. Click chemistry in peptide science: a mini-review Synthesis of clickable peptides and applications. Chim. Oggi-Chem. Today 2013, 31(2), 34-37.
52. Sun, H.B.; Peng, X.H. Template-directed fluorogenic oligonucleotide ligation using "Click" chemistry: Detection of single nucleotide polymorphism in the human p53 tumor suppressor gene. Bioconj. Chem. 2013, 24(7), 1226-1234.
53. Ingale, S.A.; Seela, F. Nucleoside and oligonucleotide pyrene conjugates with 1,2,3-triazolyl or ethynyl linkers: synthesis, duplex stability, and fluorescence changes generated by the DNA-dye connector. Tetrahedron 2014, 70(2), 380-391.
54. Haque, M.M.; Peng, X.H. DNA-associated click chemistry. Sci. China- Chem. 2014, 57(2), 215-231.
55. Serdjukow, S.; Kink, F.; Steigenberger, B.; Tomas-Gamasa, M.; Carell, T. Synthesis of gamma-labeled nucleoside 5 '-triphosphates using click chemistry. Chem. Commun. 2014, 50(15), 1861-1863.
56. Brase, S.; Gil, C.; Knepper, K.; Zimmermann, V. Organic azides: An exploding diversity of a unique class of compounds. Angew. Chem.-Int. Edit. 2005, 44(33), 5188-5240.
57. Gonzalez-Bobes, F.; Kopp, N.; Li, L.; Deerberg, J.; Sharma, P.; Leung, S.; Davies, M.; Bush, J.; Hamm, J.; Hrytsak, M. Scale-up of Azide Chemistry: A Case Study. Org. Process Res. Dev. 2012, 16(12), 2051-2057.
58. Egghart, H.C. Explosion temperatures of lead azide crystals in molten salt environments. Inorg. Chem. 1968, 7(6), 1224-1226.
59. Conrow, R.E.; Dean, W.D. Diazidomethane Explosion. Org. Process Res. Dev. 2008, 12(6), 1285-1286.
60. Churchill, D.G. Chemical structure and accidental explosion risk in the research laboratory. J. Chem. Educ. 2006, 83(12), 1798-1803.
61. Tungler, A.; Odor, E.; Bajnoczy, G. Catalytic hydrogenation of azide ion in process waste waters. Top. Catal. 2010, 53(15-18), 1153-1155.
62. Hagenbuch, J.P. Opportunities and limits of the use of azides in industrial production. Implementation of safety measures. Chimia 2003, 57(12), 773- 776.
63. Vaddula, B.R.; Gonzalez, M.A. Flow chemistry for designing sustainable chemical synthesis. Chimica. Oggi. 2013, 31(3), 18-20.
64. Puglisi, A.; Benaglia, M.; Chiroli, V. Stereoselective organic reactions promoted by immobilized chiral catalysts in continuous flow systems. Green Chem. 2013, 15(7), 1790-1813.
65. Tsubogo, T.; Ishiwata, T.; Kobayashi, S. Asymmetric carbon-carbon bond formation under continuous-flow conditions with chiral heterogeneous catalysts. Angew. Chem.-Int. Edit. 2013, 52(26), 6590-6604.
66. Wegner, J.; Ceylan, S.; Kirschning, A. Flow chemistry - a key enabling technology for (multistep) organic synthesis. Adv. Synth. Catal. 2012, 354(1), 17-57.
67. Sadler, S.; Moeller, A.R.; Jones, G.B. Microwave and continuous flow technologies in drug discovery. Expert. Opin. Drug Discov. 2012, 7(12), 1107-1128.
68. Mettler, M.S.; Stefanidis, G.D.; Vlachos, D. G. Scale-out of microreactor stacks for portable and distributed processing: coupling of exothermic and endothermic processes for syngas production. Ind. Eng. Chem. Res. 2010, 49(21), 10942-10955.
69. Cludius-Brandt, S.; Kupracz, L.; Kirschning, A. 3+2 -Cycloadditions of nitrile ylides after photoactivion of vinyl azides under flow conditions. Beilstein J. Org. Chem. 2013, 9, 1745-1750.
70. Vorontsov, A.V.; Arsentyev, A.V. Preparation of organic compounds using photocatalytic reactions. Curr. Org. Chem. 2013, 17(21), 2459-2481.
71. Knowles, J.P.; Elliott, L.D.; Booker-Milburn, K. I. Flow photochemistry: Old light through new windows. Beilstein J. Org. Chem. 2012, 8, 2025-2052.
72. Rostovtsev, V.V.; Green, L.G.; Fokin, V.V.; Sharpless, K.B. A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes. Angew. Chem.-Int. Edit. 2002, 41(14), 2596- 2599.
73. Tahir, M.N.; Qamar, R.U.; Adnan, A.; Cho, E.; Jung, S. Continuous process for click reactions using glass micro-reactor functionalized with betacyclodextrin. Tetrahedron Lett. 2013, 54(25), 3268-3273.
74. Otvos, S.B.; Georgiades, A.; Mandity, I.M.; Kiss, L.; Fulop, F. Efficient continuous-flow synthesis of novel 1,2,3-triazole-substituted betaaminocyclohexanecarboxylic acid derivatives with gram-scale production. Beilstein J. Org. Chem. 2013, 9, 1508-1516.
75. Shanmugavelan, P.; Nagarajan, S.; Sathishkumar, M.; Ponnuswamy, A.; Yogeeswari, P.; Sriram, D. Efficient synthesis and in vitro antitubercular activity of 1,2,3-triazoles as inhibitors of Mycobacterium tuberculosis. Bioorg. Med. Chem. Lett. 2011, 21(24), 7273-7276.
76. Romero, T.; Orenes, R.A.; Tarraga, A.; Molina, P. Preparation, structural characterization, electrochemistry, and sensing properties toward anions and cations of ferrocene-triazole derivatives. Organometallics 2013, 32(20), 137- 150.
77. Sakano, T.; Okano, M.; Osakada, K. Preparation of triazole-furnished ferrocene derivatives and their polymer complexes of silver(I). J. Inorg. Organomet. Polym. Mater. 2009, 19(1), 35-45.
78. Strack, M.; Langklotz, S.; Bandow, J.E.; Metzler-Nolte, N.; Albada, H.B. Silyl-based alkyne-modifying linker for the preparation of C-Terminal acetylene-derivatized protected peptides. J. Org. Chem. 2012, 77(22), 9954- 9958.
79. Palde, P.B.; Jamison, T.F. Safe and efficient tetrazole synthesis in a continuous-flow microreactor. Angew. Chem.-Int. Edit. 2011, 50(15), 3525- 3528.
80. Bogdan, A.R.; Sach, N.W. The use of copper flow reactor technology for the continuous synthesis of 1,4-disubstituted 1,2,3-triazoles. Adv. Synth. Catal. 2009, 351(6), 849-854.
81. Hu, Y.; Zhang, X.P. Selective olefination of carbonyl compounds via metalcatalyzed carbene transfer from diazo reagents. In Stereoselective Alkene Synthesis, Wang, J. Ed. Springer-Verlag Berlin: Berlin, 2012; Vol. 327, pp. 147-162.
82. Gillingham, D.; Fei, N. Catalytic X.-H insertion reactions based on carbenoids. Chem. Soc. Rev. 2013, 42(12), 4918-4931.
83. Xiao, Q.; Zhang, Y.; Wang, J.B. Diazo Compounds and N-Tosylhydrazones: Novel cross-coupling partners in transition-metal-catalyzed reactions. Accounts Chem. Res. 2013, 46(2), 236-247.
84. Kitamura, M.; Yano, M.; Tashiro, N.; Miyagawa, S.; Sando, M.; Okauchi, T. Direct Synthesis of organic azides from primary amines with 2-azido-1,3- dimethylimidazolinium hexafluorophosphate. Eur. J. Org. Chem. 2011, 2011(3), 458-462.
85. Nyffeler, P.T.; Liang, C.H.; Koeller, K.M.; Wong, C.H. The chemistry of amine-azide interconversion: Catalytic diazotransfer and regioselective azide reduction. J. Am. Chem. Soc. 2002, 124(36), 10773-10778.
86. Zeng, X.Q.; Beckers, H.; Bernhardt, E.; Willner, H. Synthesis and characterization of sulfuryl diazide, O2S(N-3)(2). Inorg. Chem. 2011, 50(17), 8679-8684.
87. Green, G.M.; Peet, N.P.; Metz, W.A. Polystyrene-supported benzenesulfonyl azide: A diazo transfer reagent that is both efficient and safe. J. Org. Chem. 2001, 66(7), 2509-2511.
88. Goddard-Borger, E.D.; Stick, R.V. An efficient, inexpensive, and shelf-stable diazotransfer reagent: Imidazole-1-sulfonyl azide hydrochloride. Org. Lett. 2007, 9(19), 3797-3800.
89. Goddard-Borger, E.D.; Stick, R.V. Additions and corrections. Org. Lett. 2011, 13(9), 2514-2514.
90. Fischer, N.; Goddard-Borger, E.D.; Greiner, R.; Klapotke, T.M.; Skelton, B.W.; Stierstorfer, J. Sensitivities of some imidazole-1-sulfonyl azide salts. J. Org. Chem. 2012, 77(4), 1760-1764.
91. United-Nations, Recommendations on the Transport of Dangerous Goods: Manual of Tests and Criteria - Amendment 1 of the 5th Revised Edition. United Nations Environment Programme: 2011.
92. Castro, V.; Banco-Canosa, J.B.; Rodriguez, H.; Albericio, F. Imidazole-1- sulfonyl azide-based diazo-transfer reaction for the preparation of azido solid supports for solid-phase synthesis. ACS Comb. Sci. 2013, 15(7), 331-334.
93. Quan, Z.J.; Xu, Q.; Zhang, Z.; Da, Y.X.; Wang, X.C. Copper-catalyzed click synthesis of functionalized 1,2,3-triazoles with 3,4-dihydropyrimidinone or amide group via a one-pot four-component reaction. Tetrahedron 2013, 69(2), 881-887.
94. Kaboudin, B.; Abedi, Y.; Yokomatsu, T. One-pot synthesis of 1,2,3-triazoles from boronic acids in water using Cu(II)-beta-cyclodextrin complex as a nanocatalyst. Org. Biomol. Chem. 2012, 10(23), 4543-4548.
95. Roy, S.; Chatterjee, T.; Islam, S.M. Polymer anchored Cu(II) complex: an efficient and recyclable catalytic system for the one-pot synthesis of 1,4- disubstituted 1,2,3-triazoles starting from anilines in water. Green Chem. 2013, 15(9), 2532-2539.
96. Appukkuttan, P.; Dehaen, W.; Fokin, V.V.; van der Eycken, E. A microwave-assisted click chemistry synthesis of 1,4-disubstituted 1,2,3- triazoles via a copper(I)-catalyzed three-component reaction. Org. Lett. 2004, 6(23), 4223-4225.