Microwave Induced Facile One-Pot Access to Diverse 2-cyanobenzothiazole-A Key Intermediate for the Synthesis of Firefly Luciferin

• Autorzy: Prajapati N. P. , Vekariya R. H. , Patel H. D.

Identyfikatory

DOI

10.18052/www.scipress.com/ILCPA.44.81

• Języki publikacji: EN

Abstrakty

EN

An eco-friendly one-step preparation of various substituted 2-cyanobenzothiazole by condensation of corresponding substituted ortho-aminothiophenol with ethyl cyanoformate, employing an effective amount of Lawesson’s reagent, under microwave irradiation (MWI) and solvent free conditions is presented. The structures of the compounds were elucidated with the aid of elemental analysis, IR, ¹H-NMR and mass spectral data. The targeted various substituted 2-cyanobenzothiazole are obtained in good yields and high purity.

Słowa kluczowe

EN

benzothiazoles; Lawesson's reagent; microwave; one-step reaction; D-luciferin

• Wydawca: Przedsiębiorstwo Wydawnictw Naukowych "DARWIN"
• Czasopismo: International Letters of Chemistry, Physics and Astronomy
• Rocznik: 2015
• Tom: Vol. 44
• Strony: 81--89
• Opis fizyczny: Bibliogr. 28 poz., wz.

Twórcy

autor

Prajapati N. P.

• Department of Chemistry, School of Sciences, Gujarat University, Ahmedabad, India

autor

Vekariya R. H.

• Department of Chemistry, School of Sciences, Gujarat University, Ahmedabad, India

autor

Patel H. D.

• Department of Chemistry, School of Sciences, Gujarat University, Ahmedabad, India

Bibliografia

• [1] E. H. White, E. Rapaport, H. H. Seliger, T. A. Hopkins, Bioorg. Chem. 1 (1971) 92-122.
• [2] V. R. Viviani, Cell. Mol. Life. Sci. 59 (2002) 1833-1850.
• [3] H. H. Seliger, W. D. McElroy, Proc. Natl. Acad. Sci. USA. 52 (1964) 75-81.
• [4] C. H. Contag, M. H. Bachmann, Annu. Rev. Biomed. Eng. 4 (2002) 235-260.
• [5] G. D. Lüker, K. E. Lüker, J. Nucl. Med. 49 (2008) 1-4.
• [6] R. A. Irgashev, A. A. Karmatsky, P. A. Slepukhin, G. L. Rusinov, V. N. Charushin, Tetrahedron Lett. 54 (2013) 5734-5738.
• [7] T. M. Potewar, K. T. Petrova, M. T. Barros, Carbohydr. Res. 379 (2013) 60-67.
• [8] R. C. Lian, M. H. Lin, M. H. Liao, J. J. Fu, Y. C. Wu, F. R. Chang, C. C. Wu, M. J. Wu, P. S. Pan, Tetrahedron. 70 (2014) 1800-1804.
• [9] M. Y. Mentese, H. Bayrak, Y. Uygun, A. Mermer, S. Ulker, S. A. Karaoglu, N. Demirbas, Eur. J. Med. Chem. 67 (2013) 230-242.
• [10] F. Messina, O. Rosati, Curr. Org. Chem. 17 (2013) 1158-1178.
• [11] P. Appukkuttan, V.P. Mehta, E. V. Van der Eycken, Chem.Soc.Rev. 39 (2010) 1467-1477.
• [12] X. Zhang, H. Jiang, D. Ye, H. Sun, H. Liu, Green Chem. 11 (2009) 1881-1888.
• [13] B. Maiti, K. Chanda, M. Selvaraju, C. C. Tseng, C. M. Sun, ACS Comb. Sci. 15 (2013) 291-297.
• [14] A. Walia, S. Kang, R. B. Silverman, J. Org. Chem. 78 (2013) 10931-10937.
• [15] E.F. Dimauro, J. M. Kennedy, J. Org. Chem. 72 (2007) 1013-1016.
• [16] R. B. Sparks, A. P. Combs, Org. Lett., 6 (2004) 2473-2475.
• [17] H. D. Patel, S. M. Divatia, E. D. Clercq, Indian J. Chem,. 52B (2013) 535-545.
• [18] S. M. Prajapati, R. H. Vekariya, K. D. Patel, S. N. Panchal, H. D. Patel, D. P. Rajani, S. Rajani, Int. Lett. Chem. Phys. Astron. 20 (2014) 195-210.
• [19] R. H. Vekariya, S. N. Panchal, K. D. Patel, H. D. Patel, Curr. Microwave Chem. (2015) DOI: 10.2174/2213335601666141023223657.
• [20] E. H. White, F. McCapra; G. F. Field, W. D. McElroy, J. Am. Chem. Soc. 83 (1961) 2402-2403.
• [21] E. H. White, F. McCapra, G. F. Field, J. Am. Chem. Soc. 85 (1963) 337-343.
• [22] S. Seto, K. Ogura, Y. Nishiyama, Bull. Chem. Soc. Jpn. 36 (1963) 331-332.
• [23] L. Bowie, J. Method Enzymol. 57 (1978) 15-28.
• [24] G. C. Stuckwisch, J. Am. Chem. Soc. 71 (1949) 3417-3417.
• [25] E. H. White, H. Woelther, G. F. Field, W. D. McElroy, J. Org. Chem. 30 (1965) 2344-2348.
• [26] N. Suzuki, T. Nomoto, N. Kanamori, B. Yoda, A. Saeki, Biosci. Biotech. Biochem. 57 (1993) 1561-1562.
• [27] Y. Toya, M. Takagi, H. Nakata, N. Suzuki, M. Isobe, T. Goto, Bull. Chem. Soc. Jpn. 65 (1992) 392-395.
• [28] P. K. Sharma, B. S. Rathore, M. Kumar, A. Fogla, Res Chem Intermed 37 (2011) 1103-1111.