Chapter 4
Applications of Nitrile Imine Derivatives
Abstract Nitrile imines have been employed in a diverse range of fields relating
to the chemical sciences. This likely originates from the pleiotropic reactivity of
the dipole, coupled with the diverse range of methods available for their generation. The overwhelming majority of these applications utilise the facile and often
orthogonal 1,3-dipolar cycloaddition between nitrile imines and electronically- or
strain-activated alkenes. More recent reports have also explored the introduction of
hydrazide synthesis through the combination of the dipole with carboxylic acids. In
addition to the adaption of nitrile imines within traditional chemical synthesis, the
dipole has also demonstrated widespread application in both bioorthogonal chemistry
and materials science as a ligation agent.
Keywords Nitrile imine · 1,3-dipole · Applications · Synthesis · 1,3-dipolar
cycloaddition · Photoclick · Bioorthogonal chemistry · Materials · Surface
chemistry · Polymer chemistry
Given the range of processes in which NI species can participate, it is unsurprising
that a number of different fields have developed a raft of applications of the dipole.
While naturally finding widespread use within general synthetic chemistry, NIs are
also prolific in bioorthogonal and materials chemistry.
4.1 General Synthesis
As has been outlined above, the reactivity profiles of NIs are extensive. This enables
the use of NIs in the synthesis of a substantial volume of compounds. By far the
most well-documented applications of NIs in synthesis is from their cycloaddition
chemistry [1–3]. Two specific areas of the dipole’s contribution to organic synthesis
should be recognised: their role in either the syntheses or late stage modification of
natural products (NPs) or biomolecules, and their roles in the syntheses of medicinally
relevant compounds.
© Springer Nature Switzerland AG 2020
C. Jamieson and K. Livingstone, The Nitrile Imine 1,3-Dipole,
https://doi.org/10.1007/978-3-030-43481-6_4
99
Applications of Nitrile Imine Derivatives
Abstract Nitrile imines have been employed in a diverse range of fields relating
to the chemical sciences. This likely originates from the pleiotropic reactivity of
the dipole, coupled with the diverse range of methods available for their generation. The overwhelming majority of these applications utilise the facile and often
orthogonal 1,3-dipolar cycloaddition between nitrile imines and electronically- or
strain-activated alkenes. More recent reports have also explored the introduction of
hydrazide synthesis through the combination of the dipole with carboxylic acids. In
addition to the adaption of nitrile imines within traditional chemical synthesis, the
dipole has also demonstrated widespread application in both bioorthogonal chemistry
and materials science as a ligation agent.
Keywords Nitrile imine · 1,3-dipole · Applications · Synthesis · 1,3-dipolar
cycloaddition · Photoclick · Bioorthogonal chemistry · Materials · Surface
chemistry · Polymer chemistry
Given the range of processes in which NI species can participate, it is unsurprising
that a number of different fields have developed a raft of applications of the dipole.
While naturally finding widespread use within general synthetic chemistry, NIs are
also prolific in bioorthogonal and materials chemistry.
4.1 General Synthesis
As has been outlined above, the reactivity profiles of NIs are extensive. This enables
the use of NIs in the synthesis of a substantial volume of compounds. By far the
most well-documented applications of NIs in synthesis is from their cycloaddition
chemistry [1–3]. Two specific areas of the dipole’s contribution to organic synthesis
should be recognised: their role in either the syntheses or late stage modification of
natural products (NPs) or biomolecules, and their roles in the syntheses of medicinally
relevant compounds.
© Springer Nature Switzerland AG 2020
C. Jamieson and K. Livingstone, The Nitrile Imine 1,3-Dipole,
https://doi.org/10.1007/978-3-030-43481-6_4
99