One-pot three-component tandem reaction: Synthesis of aryl/alkyl cyanamides libraries and their further conversion into tetrazole derivatives

References

• (a) Hu, L. Y.; Guo, J.; Mager, S. S.; Fischer, J. B.; Burke-Howie, K. J.; Durant, G. J. J. Med. Chem. 1997, 40, 4281–4289; (b) Robinson, J. R.; Brown, W. H. Can. J. Chem. 1951, 29, 1069–1074.
   PubMed Web of Science ®Google Scholar
• Stephens, R. W.; Domeier, L. A.; Todd, M. G.; Nelson, V. A. Tetrahedron Lett. 1992, 33, 733–736.
   Web of Science ®Google Scholar
• (a) Sandler, S. R.; Karo, W. In Organic Functional Group Preparations; Blomquist, A. T.; Wasserman, H., Eds.; Academic Press: New York, 1972; Vol. 3, pp 1–552; (b) Sandler, S. R.; Karo, W. In Organic Functional Group Preparations; Blomquist, A. T., Ed.; Academic Press: New York, 1971; Vol. 2, pp 1–510; (c) Nickon, A.; Fieser, L. F. J. Am. Chem. Soc. 1952, 74, 5566–5570; (d) Jia, Q.; Cai, T.; Haung, M.; Li, H.; Xian, M.; Poulos, T. L.; Wang, P. G. J. Med. Chem. 2003, 46, 2271–2276; (e) Cai, T.; Xian, M.; Wang, P. G. Bioorg. Med. Chem. Lett. 2002, 12, 1507–1510; (f) Kumar, V.; Kaushik, M. P.; Mazumdar, A. Eur. J. Org. Chem. 2008, 2008, 1910–1913; (g) Saneyoshi, M.; Tokuzen, R.; Maeda, M.; Fukuoka, F. Chem. Pharm. Bull. 1968, 16, 505–508; (h) Hu, L. Y.; Guo, J.; Magar, S.; Fischer, J. B.; Burkehowie, K. J.; Durant, G. J. J. Med. Chem. 1997, 40, 4281–4285.
   Google Scholar
• Saneyoshi, M.; Tokuzen, R.; Maeda, M.; Fukuoka, F. Chem. Pharm. Bull. 1968, 16, 505–514.
   PubMed Web of Science ®Google Scholar
• (a) Donetti, A.; Omodei-Sale, A.; Mantegani, A.; Zugna, E. Tetrahedron Lett. 1969, 39, 3327–3330; (b) Pala, G.; Mantegani, A.; Zugna, E. Tetrahedron 1970, 26, 1275–1279; (c) Curie, A. C.; Newbold, G. T.; Spring, F. S. J. Chem. Soc. 1961, 1961, 4693–4697.
   Google Scholar
• (a) Wheland, R. C.; Martin, E. L. J. Org. Chem. 1975, 40, 3101–3109; (b) Wu, Y.-Q.; Limburg, D. C.; Wikinson, D. E.; Hamiton, G. S. Org. Lett. 2000, 2, 795–798; (c) Van Leusen, A. M.; Jagt, J. C. Tetrahedron Lett. 1970, 12, 967–970; (d) Hughes, T. V.; Hammond, S. D.; Cava, M. P. J. Org. Chem. 1998, 63, 401–402; (e) Davis, W. A.; Cava, M. P. J. Org. Chem. 1983, 48, 2774–2775.
   Web of Science ®Google Scholar
• Kaupp, G.; Schmeyers, J.; Boy, J. Chem. Eur. J. 1998, 4, 2467–2474.
   Web of Science ®Google Scholar
• Van Barun, J. Ber. Dtsch. Chem. Ges. 1900, 33, 1468–1471.
   Google Scholar
• (a) Takahiro, S.; Toshihiro, I.; Kenya, K.; Katsuro, M. Tetrahedron Lett. 1973, 14, 2121–2124; (b) Mai, K.; Patil, G. Synth. Commun. 1986, 16, 1823–1827; (c) Hu, N. X.; Aso, Y.; Otsubo, T. F.; Ogura, F. Chem. Lett. 1985, 14, 603–606; (d) Sato, R.; Itoh, K.; Nishina, H.; Goto, T.; Saito, M. Chem. Lett. 1984, 13, 1913–1915.
   Google Scholar
• Bakunov, S. A.; Rukavishnikov, A. V.; Tkachev, A. V. Synthesis 2000, 2000, 1148–1151.
   Google Scholar
• Kamijo, S.; Jin, T.; Yamamoto, Y. Angew. Chem. Int. Ed. 2002, 41, 1780–1782.
   PubMed Web of Science ®Google Scholar
• Chaudhuri, K. H.; Mahajan, U. S.; Bhalerao, D. S.; Akamanchi, K. G. Synlett 2007, 2007, 2815–2818;
   Web of Science ®Google Scholar
• Wong, F. F.; Chen, C.-Y.; Yeh, M.-Y. Synlett 2006, 559–562.
   Web of Science ®Google Scholar
• Ghosh, H.; Yella, R.; Ali, A. R.; Sahoo, S. K.; Patel, B. K. Tetrahedron Lett. 2009, 50, 2407–2410.
   Web of Science ®Google Scholar
• Chen, C.-Y.; Wong, F. F.; Huang, J.-J.; Lin, S.-K.; Yeh, M.-Y. Tetrahedron Lett. 2008, 49, 6505–6508.
   Web of Science ®Google Scholar
• (a) Bowmaker, G. A.; Hanna, J. V.; Pakawatchai, C.; Skelton, B. W.; Thanyasirikul, Y.; White, A. H. Inorg. Chem. 2009, 48, 350–368; (b) Ramana, T.; Saha, P.; Das, M.; Punniyamurthy, T. Org. Lett. 2010, 12, 84–87.
   PubMed Web of Science ®Google Scholar
• (a) Batey, R. A.; Powell, D. A. Org. Lett. 2000, 2, 3237–2240; (b) Ramana, T.; Punniyamurthy, T. Chem. Eur. J. 2012, 18, 13279–13283; (c) Usharani, M.; Srinivasarao, P.; Rameshraju, R. Tetrahedron Lett. 2017, 58, 125–128.
   PubMed Web of Science ®Google Scholar
• (a) Kolb, H. C.; Sharpless, K. B. Drug Discovery Today 2003, 8, 1128–1132; (b) Moses, J. E.; Moorhouse, A. D. Chem. Soc. Rev. 2007, 36, 1249–1262; (c) Speers, A. E.; Adam, G. C.; Cravatt, B. F. J. Am. Chem. Soc. 2003, 125, 4686–4687; (d) Deiters, A.; Cropp, T. A.; Mukherji, M.; Chin, J. W.; Anderson, J. C.; Schultz, P. G. J. Am. Chem. Soc. 2003, 125, 11782–11783 (reviews on the copper-catalyzed formation of triazoles) Lutz, J. F. Angew. Chem. Int. Ed. 2007, 46, 1018–1025.
   PubMed Web of Science ®Google Scholar
• (a) Beatty, K.; Xie, F.; Wang, Q.; Tirrell, D. A. J. Am. Chem. Soc. 2005, 127, 14150–14151; (b) Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2004, 126, 10598–10599; (c) Oh, K.; Guan, Z. Chem. Commun. 2006, 3069–3071; (d) Seela, F.; Sirivolu, V. R.; Chittepu, P. Bioconjugate Chem. 2008, 19, 211.
   PubMed Web of Science ®Google Scholar
• Li, H.; Cheng, F.; Duft, A. M.; Adronov, A. J. Am. Chem. Soc. 2005, 127, 14518–14524.
   PubMed Web of Science ®Google Scholar
• Parrish, B.; Breitenkamp, R. B.; Emrick, T. D. J. Am. Chem. Soc. 2005, 127, 7404–7405; (b) Malkoch, M.; Schleicher, K.; Drockenmuller, E.; Hawker, C. J.; Russell, T. P.; Wu, P.; Fokin, V. V. Macromolecules 2005, 38, 3663–3667.
   PubMed Web of Science ®Google Scholar
• (a) Wamhoff, H. Comprehensive Organic Reactions in Aqueous Media. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R.; Rees, C. W.; Eds.; Pergamon: Oxford, 1984; Vol. 5, pp 669–732; (b) Dehne, H. In Methoden der Organischen Chemie (Houben-Weyl); Schumann, E., Ed.; Thieme: Stuttgart, 1994; Vol. E8d, pp 305–405; (c) Fan, W. Q.; Katritzky, A. R. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Elsevier Science: Oxford, 1996; Vol. 12, 1–126.
   Google Scholar
• Padwa, A. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991, 1069; (b) Huisgen, R. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: NewYork, 1984; pp 1; (c) Huisgen, R. Pure Appl. Chem. 1989, 61, 613; (d) Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863–910.
   Google Scholar
• (a) Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057–3064; (b) Labbe, G. Bull. Soc. Chem. Belg. 1984, 93, 579–583; (c) Meldal, M.; Tornøe, C. W. Chem. Rev. 2008, 108, 2952–3015.
   PubMed Web of Science ®Google Scholar
• Wu, P.; Feldman, A. K.; Nugent, A. K.; Hawker, C. J.; Scheel, A.; Voit, B.; Pyun, J.; Frechet, J. M.; Sharpless, K. B.; Fokin, V. V. Angew. Chem. Int. Ed. 2004, 43, 3928–3930.
   PubMed Web of Science ®Google Scholar
• (a) Rodionov, V. O.; Presolski, S. I.; Gardinier, S.; Lim, Y.-H.; Finn, M. G. J. Am. Chem. Soc. 2007, 129, 12696–12704; (b) Rodionov, V. O.; Presolski, S. I.; Diaz, D.; Fokin, V. V.; Finn, M. G. J. Am. Chem. Soc. 2007, 129, 12705–12710; (c) Lewis, W. G.; Magallon, F. G.; Fokin, V. V.; Finn, M. G. J. Am. Chem. Soc. 2004, 126, 9152–9153.
   PubMed Web of Science ®Google Scholar
• Diez-Gonzalez, S.; Correa, A.; Cavallo, L.; Nolan, S. P. Chem. Eur. J. 2006, 12, 7558–7564.
   PubMed Web of Science ®Google Scholar
• Miao, T.; Wang, L. Synthesis 2008, 2008, 363–368.
   Web of Science ®Google Scholar
• (a) Chassaing, S.; Kumarraja, M.; Sido, A. S. S.; Pale, P.; Sommer, J. Org. Lett. 2007, 9, 883–886; (b) Chassaing, S.; Sido, A. S.; Alix, A.; Kumarraja, M.; Pale, P.; Sommer, J. Chem. Eur. J. 2008, 14, 6713–1719.
   PubMed Web of Science ®Google Scholar
• Girard, C.; Onen, E.; Aufort, M.; Beauviere, S.; Samson, E.; Herscovici, J. Org. Lett. 2006, 8, 1689–1692.
   PubMed Web of Science ®Google Scholar
• Lipshutz, B. H.; Taft, B. R. Angew. Chem. Int. Ed. 2006, 45, 8235–8238.
   PubMed Web of Science ®Google Scholar
• (a) Kolarovic, A.; Schnurch, M.; Mihovilovic, M. D. J. Org. Chem. 2011, 76, 2613–2618; (b) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem. Int. Ed. 2002, 41, 2596–2599.
   PubMed Web of Science ®Google Scholar
• Brik, A.; Muldoon, J.; Lin, Y.-C.; Elder, J. H.; Goodsell, D. S.; Olson, A. J.; Fokin, V. V.; Sharpless, K. B.; Wong, C.-H. ChemBioChem 2003, 4, 1246–1250.
   PubMed Web of Science ®Google Scholar
• Wang, Q.; Chan, T. R.; Higraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192–3193.
   PubMed Web of Science ®Google Scholar
• (a) Wittenberger, S. Org. Prep. Proced. Int. 1994, 26, 499–502; (b) Herr, R. J. Biorg. Med. Chem. 2002, 10, 3379–3383.
   Web of Science ®Google Scholar
• (a) Ek, F.; Wistrandand, L.-G.; Frejd, T. Tetrahedron 2003, 59, 6759–6762; (b) Flippin, L. A. Tetrahedron Lett. 1991, 32, 6857–6860; (c) Rhonnstad, P.; Wensbo, D. Tetrahedron Lett. 2002, 43, 3137–3140.
   Web of Science ®Google Scholar
• (a) Ford, R. E.; Knowles, P.; Lunt, E.; Marshall, S. M.; Penrose, A. J.; Ramsden, C. A.; Summers, A. J. H.; Walker, J. L.; Wright, D. E. J. Med. Chem. 1986, 29, 538–549; (b) Peet, N. P.; Baugh, L. E.; Sundler, S.; Lewis, J. E.; Matthews, E. H.; Olberding, E. L.; Shah, D. N. J. Med. Chem. 1986, 29, 2403–2409.
   PubMed Web of Science ®Google Scholar
• Girijavallabhan, V. M.; Pinto, P. A.; Genguly, A. K.; Versace, R. W. Eur. Patent EP274867, 1988; Chem. Abstr. 1989, 110, 23890–23894.
   Google Scholar
• (a) Akimoto, H.; Ootsuand, K.; Itoh, F. Eur. Patent EP530537, 1993; Chem. Abstr. 1993, 119, 226417; (b) Taveras, A. G.; Mallams, A. K.; Afonso, A. Int. patent WO9811093, 1998; Chem. Abstr. 1998, 128, 230253.
   Google Scholar
• Yamazaki, K.; Hasegawa, H.; Umekawa, K.; Ueki, Y.; Ohashi, N.; Kanaoka, M. Bioorg. Med. Chem. Lett. 2002, 12, 1275–1278.
   PubMed Web of Science ®Google Scholar
• Habich, D. Synthesis 1992, 1992, 358–360;
   Google Scholar
• Vieira, E.; Huwyler, S.; Jolidon, S.; Knoflach, F.; Mutel, J.; Wichmann, J. Bioorg. Med. Chem. Lett. 2005, 15, 4628–4632.
   PubMed Web of Science ®Google Scholar
• (a) Herr, R. J. Bioorg. Med. Chem. 2002, 10, 3379–3383; (b) Butler, R. N. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon, E: New York, 1994; Vol. 4, pp 621–628; (c) Burger, A. Prog. Drug. Res. 1991, 37, 287–292; (d) Voitekhovich, S. V.; Gaponikand, P. N.; Ivashkevich, O. A. Russ. Chem. Rev. 2002, 71, 721–728; (e) Thornber, C. W. Chem. Soc. Rev. 1979, 8, 563–580; (f) Singh, H.; Chawla, A. S.; Kapoor, V. K.; Paul, D.; Malhotra, R. K. Prog. Med. Chem. 1980, 17, 151–156.
   PubMed Web of Science ®Google Scholar
• Kye, J. S.; Ki, D. K.; Kyung, H. Y.; Dong, C. K.; Dong, J. K.; Sang, W. P. Bioorg. Med. Chem. Lett. 2000, 10, 1421–1425.
   PubMed Web of Science ®Google Scholar
• Ghosh, H.; Yella, R.; Ali, A. R.; Sahoo, S. K.; Patel, B. K. Tetrahedron Lett. 2009, 50, 2407–2410.
   Web of Science ®Google Scholar