Benzotriazole: An Ideal Synthetic Auxiliary

Abstract

Benzotriazole is a synthetic auxiliary that offers many advantages. It is inexpensive, odorless, and stable. A benzotriazole group is easily introduced, activates molecules towards numerous transformations, and can be removed easily at the end of the reaction sequence. This Concept provides some recent examples of the synthetic application of benzotriazole methodology and is intended to draw attention to the versatile applications of benzotriazole in organic chemistry.

A Versatile Direct Approach to ortho‐Substituted Azobenzenes from Benzotriazoles

“…[12] The existence of a free diazonium species in equilibrium with the 1,2,3-triazole ring is known in the parent 1,2,3-triazole substituted with a sulfonyl group at N1. This equilibrium was confirmed by 1 H NMR spectroscopic studies. [13] In the benzotriazole series two compounds can be conceived to be in equilibrium with the diazo structure.…”

“…[1] Benzotriazole is an inexpensive, stable, and biologically innocuous compound [1a] which can be easily introduced into organic molecules. After conferring its multiple activating influences for carrying out precise transformation reactions, it can be easily removed and can generally be recycled.…”

The synthesis and energetic properties of pyridinium and triazolium nitrobenzoyl ylids

“…6 Benzotriazole is a synthetic auxiliary that offers many advantages in organic synthesis since it is easy to introduce, activates molecules towards numerous transformations, and can be removed easily at the end of a reaction. 7 In a continuing effort to explore the chemistry of compounds that are safe to handle and more cost-efficient to produce, we investigated the synthesis of nitro-substituted N-benzoylimides as potential candidates for energetic materials using acylbenzotriazoles rather than acid chlorides as the reactive starting materials. …”

Microwave-assisted synthesis of some new coumarin derivatives including 1,2,4-triazol-3-one and investigation of their biological activities

“…44 In this context, 3-(1H-benzotriazol-1-ylcarbonyl)-2H-chromen-2-one (7a) has been used for the preparation of some biologically active and fluorescent compounds. 43 In particular, this compound has been used with certain amino acids, peptides, and thioles to prepare coumarin-labelled compounds.…”