Issue 7, 1995

Synthesis of 2-substituted benzoxazoles and benzimidazoles based on mass spectral ortho interactions

Abstract

The ortho interactions of the hydroxy and amino groups with the amide function in N-(2-hydroxyphenyl)and N-(2-aminophenyl)-benzamides on electron impact lead to the elimination of H2O from the molecular ions resulting in the formation of 2-substituted benzoxazoles and benzimidazole radical cations, respectively. This mass spectrometric reaction has been successfully mimicked in the laboratory to synthesise these heterocyclic compounds in excellent yields by the thermolysis of the corresponding N-(2-hydroxyphenyl)- and N-(2-aminophenyl)-benzamides. The mechanisms and ion structures proposed in the mass spectral study are supported by high-resolution data, B/E and B2/E linked-scan spectra, Collision-Activation-Decomposition (CAD)-B/E linked-scan spectra, chemical substitution and 2H-labelling.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1995, 1497-1501

Synthesis of 2-substituted benzoxazoles and benzimidazoles based on mass spectral ortho interactions

D. V. Ramana and E. Kantharaj, J. Chem. Soc., Perkin Trans. 2, 1995, 1497 DOI: 10.1039/P29950001497

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements