The Effect of Deactivating Groups in the Formation of Some Biologically Important Lactams (Isatins) and their Further Derivatization

Authors

  • Mohammad M Hossain Department of Chemistry, Jahangirnagar University, Savar, Dhaka-1342
  • Noor N Ferdous Department of Chemistry, Jahangirnagar University, Savar, Dhaka-1342
  • Md Hasan Muhib Department of Chemistry, Jahangirnagar University, Savar, Dhaka-1342
  • Md Sultan Alam Department of Chemistry, Jahangirnagar University, Savar, Dhaka-1342
  • Md Rabiul Islam Department of Chemistry, Jahangirnagar University, Savar, Dhaka-1342
  • Md Abdul Hai Department of Chemistry, Jahangirnagar University, Savar, Dhaka-1342
  • Wajdi Zoghaib Department of Chemistry, Sultan Qaboos University, Al Khod, P. C. 123, Sultanate of Oman

DOI:

https://doi.org/10.3329/jbcs.v25i1.11771

Keywords:

Important, Lactams

Abstract

Treatment of different aromatic primary amines (7a-b) with chloral hydrate andhydroxylamine hydrochloride under microwave (MW) conditions afforded correspondingisonitrosoacetanilides (6a-b). These intermediate compounds (6a-b) were cyclized inconc. H2SO4 medium to give cyclic amides (5a-b) by means of elcetrophilicaromatic substitution reaction. The microwave (MW) mediated treatment of compound5a with thiosemicarbazide afforded the corresponding Schiff-base 4a, which undergoescyclization to give thiadiazoline (1). Beside, compound 4a was also treated with aq KOHsolution under MW condition to give triazinothione (3). The Sn-HCl mediatedreduction of compound 3 afforded the corresponding 6-aminothione (2). On the otherhand, compound 5b was treated with o-phenylenediamine under MW condition to givethe corresponding quinoxaline derivative 4b in excellent yield.

DOI: http://dx.doi.org/10.3329/jbcs.v25i1.11771

Journal of Bangladesh Chemical Society, Vol. 25(1), 46-52, 2012

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Published

2012-09-03

How to Cite

Hossain, M. M., Ferdous, N. N., Muhib, M. H., Alam, M. S., Islam, M. R., Hai, M. A., & Zoghaib, W. (2012). The Effect of Deactivating Groups in the Formation of Some Biologically Important Lactams (Isatins) and their Further Derivatization. Journal of the Bangladesh Chemical Society, 25(1), 46–52. https://doi.org/10.3329/jbcs.v25i1.11771

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