Synlett 2025; 36(19): 3250-3254
DOI: 10.1055/a-2680-2213
Letter

Unravelling the Synthesis of Benzo[d]imidazo[2,1-b]thiazoles via MnO2/I2-Catalyzed Ortoleva-King Type Approach

Autoren

  • Thaipparambil Aneeja

    1   School of Chemical Sciences, Mahatma Gandhi University, PD Hills, Kottayam, Kerala, India (Ringgold ID: RIN29318)
  • Padinjare Veetil Saranya

    1   School of Chemical Sciences, Mahatma Gandhi University, PD Hills, Kottayam, Kerala, India (Ringgold ID: RIN29318)
  • Gopinathan Anilkumar

    1   School of Chemical Sciences, Mahatma Gandhi University, PD Hills, Kottayam, Kerala, India (Ringgold ID: RIN29318)
    2   Institute for Integrated Programs and Research in Basic Sciences (IIRBS), Mahatma Gandhi University, PD Hills, Kottayam, Kerala, India (Ringgold ID: RIN29318)

Funding Information No funding data available.


Graphical Abstract

Dedication

Dedicated with profound reverence to Dr. Vijay Nair on the occasion of his first death anniversary.

Abstract

The first MnO2/I2-catalyzed one-pot synthesis of benzo[d]imidazo[2,1-b]thiazole from 2-aminobenzothiazole and aryl methyl ketone has been described. This methodology involves the in situ generation of α-iodoketone from aryl methyl ketone in the presence of a catalytic amount of molecular iodine. An array of aromatic ketones and 2-aminobenzothiazoles were compatible with this strategy, providing diverse fused benzoimidazothiazoles in moderate to good yields.



Publikationsverlauf

Eingereicht: 24. Mai 2025

Angenommen nach Revision: 08. August 2025

Artikel online veröffentlicht:
26. August 2025

© 2025. Thieme. All rights reserved.

Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany

 
  • References

  • 1 Rassokhina IV, Tikhonova TA, Kobylskoy SG. et al. J Org Chem 2017; 82: 9682-9692
  • 2 Ager IR, Barnes AC, Danswan GW. et al. J Med Chem 1988; 31: 1098-1115
  • 3 Furlan A, Colombo F, Kover A, Issaly N. Eur J Med Chem 2012; 47: 239-254
  • 4 Palkar M, Noolvi M, Sankangoud R, Maddi V, Gadad A, Nargund LVG. Arch Pharm 2010; 343: 353-359
  • 5 Al-Tel TH, Al-Qawasmeh RA, Zaarour R. Eur J Med Chem 2011; 46: 1874-1881
  • 6 Chao Q, Sprankle KG, Grotzfeld RM. et al. J Med Chem 2009; 52: 7808-7816
  • 7 Farag AM, Mayhoub AS, Barakat SE, Bayomi AH. Bioorg Med Chem 2008; 16: 4569-4578
  • 8 Patel HK, Grotzfeld RM, Lai AG. et al. Bioorg Med Chem Lett 2009; 19: 5182-5185
  • 9 Chitti S, Calster KV, Cappoen D. et al. RSC Adv 2022; 12: 22385-22401
  • 10 Gill RK, Rawal RK, Bariwal J. J Arch Pharm 2015; 348: 155-178
  • 11 Balwe SG, Jeong YT. RSC Adv 2016; 6: 107225-107232
  • 12 Wang J, Li J, Zhu Q. Org Lett 2015; 17: 5336-5339
  • 13 Mukku N, Maiti B. RSC Adv 2020; 10: 770-778
  • 14 Mishra S, Monir K, Mitra S, Hajra A. Org Lett 2014; 16: 6084-6087
  • 15 Pham PT, Nguyen DK, Phan NTS, Le M-V, Nguyen TT. RSC Adv 2023; 13: 3341-3345
  • 16 Aneeja T, Philip RM, Anilkumar G. Results Chem 2022; 4: 100474
  • 17 Liu W, Ackermann L. ACS Catal 2016; 6: 3743-3752
  • 18 Cano R, Mackey K, McGlacken GP. Catal Sci Technol 2018; 8: 1251-1266
  • 19 Yang X, Wang C. Chem Asian J 2018; 13: 2307-2315
  • 20 Gawali SS, Pandia BK, Pal S, Gunanathan C. ACS Omega 2019; 4: 10741-10754
  • 21 Lane BS, Vogt M, DeRose VJ, Burgess K. J Am Chem Soc 2002; 124: 11946-11954
  • 22 Snider BB, Mohan R, Kates SA. J Org Chem 1985; 50: 3659-3661
  • 23 Allard S, Gunten U, Sahli E, Nicolau R, Gallard H. Water Res 2009; 43: 3417-3426