Benzotriazole: A Versatile Synthetic Auxiliary
Journal Title: Archives of Organic and Inorganic Chemical Sciences - Year 2018, Vol 2, Issue 1
Abstract
Benzotriazole (BtH) is particularly versatile synthetic auxiliary because of its attractive properties. Benzotriazole can be easily inserted into molecules and equally can also act as a good leaving group. This molecule is a weak acid (pKa 8.2) as well as weak base (pKa < 0) and because of this acid-base property of benzotriazole. This molecule also shows not only electron donating but also electron attracting ability, which leads to various synthetic applications. In 1980, benzotriazole was first reported as synthetic auxiliary in organic chemistry [1]. Since then benzotriazole is used in the construction of various monocyclic and bicyclic heterocyclic compounds which are difficult to prepare by other methods [2-5]. Heterocycles are important class of compounds. Benzotriazole extensively used for the synthesis of various heterocycles. 1-Aza- 1,3-bis(triphenyl phosphoranylidene)propane synthesized from N-((1H-benzo[d][1,2,3]triazol-1-yl)methyl)-1,1,1-triphenyH5- phosphanimine and methylene triphenyl phosphorane in presence of n-butyllithium, used as potential building block for the synthesis of heterocycles like 3H-benzo[c] azepine and 2,3-disubstituted pyrroles [6].2-Substituted benzothiazoles are well known for their biological properties with numerous accounts listing their synthesis [7]. Recently, benzotriazole technology was used in water as a one-pot approach to synthesize 2-peptidyl benzothiazole in excellent yield without any detectable racemization [8]. The effectiveness of this approach relies in the fact that it neither required any additional reagents nor catalyst for completion (Figure 1-3).
Authors and Affiliations
Siva S Panda
Keywords
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- EP ID EP602952
- DOI 10.32474/AOICS.2018.02.000129
- Views 73
- Downloads 0
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