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

Prajapati, Neelam P.; Vekariya, Rajesh H.; Patel, Hitesh D.

doi:10.18052/www.scipress.com/ILCPA.44.81

ILCPA > ILCPA Volume 44 > Microwave Induced Facile One-Pot Access to Diverse...

< Back to Volume

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

Full Text PDF

Abstract:

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.

Info:

Periodical:

International Letters of Chemistry, Physics and Astronomy (Volume 44)

Pages:

81-89

DOI:

https://doi.org/10.18052/www.scipress.com/ILCPA.44.81

Citation:

N. P. Prajapati et al., "Microwave Induced Facile One-Pot Access to Diverse 2-Cyanobenzothiazole-A Key Intermediate for the Synthesis of Firefly Luciferin", International Letters of Chemistry, Physics and Astronomy, Vol. 44, pp. 81-89, 2015

Online since:

January 2015

Authors:

Neelam P. Prajapati, Rajesh H. Vekariya, Hitesh D. Patel

Keywords:

Benzothiazoles, D-Luciferin, Lawesson’s Reagent, Microwave, One-Step Reaction

Export:

RIS, BibTeX, Text

Distribution:

Open Access

This work is licensed under a
Creative Commons Attribution 4.0 International License

References:

E. H. White, E. Rapaport, H. H. Seliger, T. A. Hopkins, Bioorg. Chem. 1 (1971) 92-122.

V. R. Viviani, Cell. Mol. Life. Sci. 59 (2002) 1833-1850.

H. H. Seliger, W. D. McElroy, Proc. Natl. Acad. Sci. USA. 52 (1964) 75-81.

C. H. Contag, M. H. Bachmann, Annu. Rev. Biomed. Eng. 4 (2002) 235-260.

G. D. Lüker, K. E. Lüker, J. Nucl. Med. 49 (2008) 1-4.

R. A. Irgashev, A. A. Karmatsky, P. A. Slepukhin, G. L. Rusinov, V. N. Charushin, Tetrahedron Lett. 54 (2013) 5734-5738.

T. M. Potewar, K. T. Petrova, M. T. Barros, Carbohydr. Res. 379 (2013) 60-67.

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.

M. Y. Mentese, H. Bayrak, Y. Uygun, A. Mermer, S. Ulker, S. A. Karaoglu, N. Demirbas, Eur. J. Med. Chem. 67 (2013) 230-242.

F. Messina, O. Rosati, Curr. Org. Chem. 17 (2013) 1158-1178.

P. Appukkuttan, V.P. Mehta, E. V. Van der Eycken, Chem. Soc. Rev. 39 (2010) 14671477.

X. Zhang, H. Jiang, D. Ye, H. Sun, H. Liu, Green Chem. 11 (2009) 1881-1888.

B. Maiti, K. Chanda, M. Selvaraju, C. C. Tseng, C. M. Sun, ACS Comb. Sci. 15 (2013) 291-297.

A. Walia, S. Kang, R. B. Silverman, J. Org. Chem. 78 (2013) 10931-10937.

E.F. Dimauro, J. M. Kennedy, J. Org. Chem. 72 (2007) 1013-1016.

R. B. Sparks, A. P. Combs, Org. Lett., 6 (2004) 2473-2475.

H. D. Patel, S. M. Divatia, E. D. Clercq, Indian J. Chem,. 52B (2013) 535-545.

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.

R. H. Vekariya, S. N. Panchal, K. D. Patel, H. D. Patel, Curr. Microwave Chem. (2015) DOI: 10. 2174/2213335601666141023223657.

E. H. White, F. McCapra; G. F. Field, W. D. McElroy, J. Am. Chem. Soc. 83 (1961) 2402-2403.

E. H. White, F. McCapra, G. F. Field, J. Am. Chem. Soc. 85 (1963) 337-343.

S. Seto, K. Ogura, Y. Nishiyama, Bull. Chem. Soc. Jpn. 36 (1963) 331-332.

L. Bowie, J. Method Enzymol. 57 (1978) 15-28.

G. C. Stuckwisch, J. Am. Chem. Soc. 71 (1949) 3417-3417.

E. H. White, H. Woelther, G. F. Field, W. D. McElroy, J. Org. Chem. 30 (1965) 23442348.

N. Suzuki, T. Nomoto, N. Kanamori, B. Yoda, A. Saeki, Biosci. Biotech. Biochem. 57 (1993) 1561-1562.

Y. Toya, M. Takagi, H. Nakata, N. Suzuki, M. Isobe, T. Goto, Bull. Chem. Soc. Jpn. 65 (1992) 392-395.

P. K. Sharma, B. S. Rathore, M. Kumar, A. Fogla, Res Chem Intermed 37 (2011) 11031111. ( Received 11 December 2014; accepted 21 December 2014 ).

Show More Hide

Cited By:

[1] S. Kanie, T. Nishikawa, M. Ojika, Y. Oba, "One-pot non-enzymatic formation of firefly luciferin in a neutral buffer from p-benzoquinone and cysteine", Scientific Reports, Vol. 6, 2016

DOI: https://doi.org/10.1038/srep24794

[2] S. Kanie, R. Nakai, M. Ojika, Y. Oba, "2- S -cysteinylhydroquinone is an intermediate for the firefly luciferin biosynthesis that occurs in the pupal stage of the Japanese firefly, Luciola lateralis", Bioorganic Chemistry, 2018

DOI: https://doi.org/10.1016/j.bioorg.2018.06.028