p-TsOH-mediated, Versatile, and Efficient Approach for the Synthesis of Triazolyl-Carbazoles from Nitrovinylcarbazoles and Azide via 1, 3-Dipolar Cycloaddition
Vijay Kumar Reddy Avula
Department of Chemistry, Sri Venteswara University, Tiruprti, 517502 Andhra Pradesh, India
Centre for Chemical Sceince and Technology, IST, Jawaharlal Nehru Technological University Hyderabad, Kukatpally, 500085 Telangana, India
Search for more papers by this authorSwetha Vallela
Centre for Chemical Sceince and Technology, IST, Jawaharlal Nehru Technological University Hyderabad, Kukatpally, 500085 Telangana, India
Search for more papers by this authorJaya Shree Anireddy
Centre for Chemical Sceince and Technology, IST, Jawaharlal Nehru Technological University Hyderabad, Kukatpally, 500085 Telangana, India
Search for more papers by this authorCorresponding Author
Naga Raju Chamarthi
Department of Chemistry, Sri Venteswara University, Tiruprti, 517502 Andhra Pradesh, India
E-mail: [email protected]Search for more papers by this authorVijay Kumar Reddy Avula
Department of Chemistry, Sri Venteswara University, Tiruprti, 517502 Andhra Pradesh, India
Centre for Chemical Sceince and Technology, IST, Jawaharlal Nehru Technological University Hyderabad, Kukatpally, 500085 Telangana, India
Search for more papers by this authorSwetha Vallela
Centre for Chemical Sceince and Technology, IST, Jawaharlal Nehru Technological University Hyderabad, Kukatpally, 500085 Telangana, India
Search for more papers by this authorJaya Shree Anireddy
Centre for Chemical Sceince and Technology, IST, Jawaharlal Nehru Technological University Hyderabad, Kukatpally, 500085 Telangana, India
Search for more papers by this authorCorresponding Author
Naga Raju Chamarthi
Department of Chemistry, Sri Venteswara University, Tiruprti, 517502 Andhra Pradesh, India
E-mail: [email protected]Search for more papers by this authorAbstract
An efficient method for the synthesis of N-alkylated 3-(1-benzyl-1H-1,2,3-triazole-4-yl)-9H-carbazoles (5, 6, 7, 8, 9, 10) and 9-ethyl-3,6-di(1H-1,2,3-triazole-4-yl)-9H-carbazole (13) has been developed from nitroolefines. The effects of catalyst and solvent on these reactions have been investigated. p-TsOH-THF was found to be the best system for this reaction. Various triazolyl-carbazoles were prepared in good to excellent yields.
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References and Notes
- 1Chakraborty, D. P.; Herz, W. In Carbazole Alkaloids in Progress in the Chemistry of Organic Natural Products; H. Grisebach; G. W. Kirby; C. Tamm, Eds.; Springer Verlag Wien: New York, 1977; Vol 34, p 299.
- 2Kapil, R. S.; Manske, R. Carbazole Alkaloids; Academic Press: New York, 1971; Vol 13, p 273.
- 3Joule, J. A.; Katritzky, A. R. Advances in Heterocyclic Chemistry; Academic Press: Orlando, 1984; Vol 35, p 83.
- 4Pindur, U. Chimia 1990, 44, 406.
- 5Knolker, H. J.; Reddy, K. R. Chem Rev 2002, 102, 4303.
- 6Hewlins, M. J. E.; Oliveira-Campos, A. M.; Shannon, P. V. R. Synthesis 1984 289.
- 7Pindur, U.; Haber, M.; Sattler, K. J Chem Educ 1993, 70, 263.
- 8Segall, A.; Pappa, H.; Pizzarno, M. T.; Radice, M.; Amoroso, A.; Gutkind, G. IL Farmaco 1996, 51, 513.
- 9Akrami, H.; Mirjalili, B. F.; Khoobi, M.; Moradi, A.; Nadri, H.; Emami, S.; Foroumadi, A.; Vosooghi, M.; Shafiee, A. Arch Pharm Chem Life Sci 2015, 348, 366.
- 10Aufort, M.; Herscovici, J.; Bouhours, P.; Moreau, N.; Girard, C. Bioorg Med Chem Lett 2008, 18, 1195.
- 11Gaur, M.; Goel, M.; Sridhar, L.; Ashok, T. D. S.; Prabhakar, S.; Dureja, P.; Raghunathan, P.; Eswaran, S. V. Monatsh Chem 2012, 143, 283.
- 12Dhooghe, M.; Vandekerckhove, S.; Mollet, K.; Vervisch, K.; Dekeukeleire, S.; Lehoucq, L.; Latedgan, C.; Smith, P. J.; Chibale, K.; Kimpe, N. D. Beilstein J Org Chem 2011, 7, 1745.
- 13Salmon, A. J.; Williams, M. L.; Wu, Q. K.; Morrizzi, J.; Gregg, D.; Charman, S. A.; Vullo, D.; Supuran, C. T.; Poulsan, S. A. J Med Chem 2012, 55, 5506.
- 14Buckle, D. R.; Rockell, C. J. M.; Smith, H.; Spicer, B. A. J Med Chem 1986, 29, 2262.
- 15Whiting, M.; Muldoon, J.; Lin, Y. C.; Silverman, M. S.; Lindstron, W.; Olson, A. J.; Kolb, H. C.; Finn, M. G.; Sharpless, K. B.; Elder, J. H.; Fokin, V. V. Angew Chem Int Ed 2006, 45, 1435.
- 16Labadie, G. R.; De la Iqlesia, A.; Morbidoni, H. R. Mol Divers 2011, 15, 1017.
- 17Duan, H.; Sun, X.; Liao, W.; Petersen, J. L.; Shi, X. Org Lett 2008, 10, 4113.
- 18 R. Huisgen; A. Padwa (Eds) 1,3-Dipolar Cycloaddition Chemistry; Wiley: New York, 1984, 1, 1.
- 19(a) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew Chem Int Ed 2002, 41, 2596;
10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4 CAS PubMed Web of Science® Google Scholar(b) Tornøe, C. W.; Christensen, C.; Meldal, M. J Org Chem 2002, 67, 3057.
- 20(a) Zhang, L.; Chen, X.; Xue, P.; Sun, H. H. Y.; Williams, I. D.; Sharpless, K. B.; Fokin, V. V.; Jia, G. J Am Chem Soc 2005, 127, 15998; (b) Kamijo, S.; Jin, T.; Huo, Z.; Yamamoto, Y. J Am Chem Soc 2003, 125, 7786; (c) Wu, Y.-M.; Deng, J.; Li, Y.; Chen, Q.-Y. Synthesis 2005 1314.
- 21Lu, L.; Wu, J.; Yang, C. J Chin Chem Soc 2008, 55, 414.
- 22Barluenga, J.; Valdes, C.; Beltrn, G.; Escribano, M.; Aznar, F. Angew Chem 2006, 118, 7047.
10.1002/ange.200601045 Google Scholar
- 23Zhu, W.; Ma, D. Chem Commun 2004, 7, 888.
- 24Jin, T.; Kamijo, S.; Yamamoto, Y. Eur J Org Chem 2004, 3789.
- 25Wang, X.; Kuang, C.; Yang, Q. Eur J Org Chem 2012, 2012, 424.
- 26Huanga, Q.; Zhenga, M.; Yang, S.; Kuang, C.; Yu, C.; Yang, Q. Eur J Med Chem 2011, 46, 5680.
- 27Xue-Jing, Q.; Zhi-Hui, R.; Yao-Yu, W.; Zheng-Hui, G. Org Lett 2014, 16, 5728.
- 28Dey, G.; GuptaMukherjee, A. T.; Gaur, P.; Chaudhary, A.; Mukhopadhyay, S. K.; Nandi, C. K.; Ghosh, S. ACS Appl Mater Interfaces 2014, 6, 10231.
- 29Shi, H.; Dai, J.; Li Shi, L.; Xua, Z.; Zhoua, Y.; Zhanga, W.; Zhoua, C. D. Spectrochim Acta 2012, 93, 19.
- 30Goverdhan, S.; Perumal, Y.; Dharmarajan, S.; Srinivas, K. Bioorg Med Chem Lett 2015, 25, 485.
- 31Pereira, V. L. P.; André, L.; da Moura, S.; Vieira, D. P. P.; Carvalho, L. L.; Torres, E. R. B.; da Costa, J. S. Beilstein J Org Chem 2013, 9, 832.
- 32Li, L.; Wu, Y.; Zhou, Q.; He, C. J Phys Org Chem 2012, 25, 362.
- 33Isoshima, T.; Wada, T.; Zhang, Y.; Brouyere, E.; Bredas, J.; Sasabe, H. J Chem Phys 1996, 104, 2467.