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Free Radical Synthetic Protocol for Benzothiazoles via Ring Opening of Benzotriazole: A Two‐step Organic Chemistry Experiment for Undergraduate and Postgraduate Students
Author(s) -
Singh Anoop S.,
Mishra Nidhi,
Yadav Mangal S.,
Tiwari Vinod K.
Publication year - 2019
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3405
Subject(s) - chemistry , benzotriazole , reagent , moiety , organic synthesis , ring (chemistry) , nucleophilic substitution , combinatorial chemistry , cleavage (geology) , organic chemistry , nucleophile , catalysis , geotechnical engineering , fracture (geology) , engineering
The utility and advantages of benzotriazole methodology have been described for the practical synthesis of benzothiazoles. The two‐step synthetic procedure includes nucleophilic acyl substitution followed by benzotriazole ring cleavage under the free radical condition and subsequent cyclization via elimination of molecular nitrogen (N 2 ). This protocol requires cheap and readily available reagents, and moreover easy to handle, thus can be used to teach undergraduate and postgraduate students about the importance of benzotriazole moiety in organic synthesis, ring cleavage chemistry, cyclization reactions, and use of industrial waste in free radical reactions. Students can also learn some important and common techniques useful in organic chemistry such as monitoring of organic reaction using thin‐layer chromatography and UV, microwave (MW) technique for the synthesis, and column chromatography for the product isolation and structure determination through NMR, MS, and IR spectral analysis of the pure compounds.