<span style="font-size:12.0pt;font-family: "Times New Roman";mso-fareast-font-family:"Times New Roman";mso-ansi-language: EN-IN;mso-fareast-language:EN-IN;mso-bidi-language:AR-SA" lang="EN-IN">Mass spectrometer as a probe in the synthesis of 2-substituted-4(3<i style="mso-bidi-font-style: normal">H</i>)-quinazolinones</span>

Abstract

<span style="font-size:12.0pt;font-family: " times="" new="" roman";mso-fareast-font-family:"times="" roman";mso-ansi-language:="" en-in;mso-fareast-language:en-in;mso-bidi-language:ar-sa"="" lang="EN-IN">The <i>ortho </i>interaction of the amide function with the <i>N-</i><span style="mso-bidi-font-style:italic">aroyl<i> </i>group in 2-(substituted benzamido)benzamides <b style="mso-bidi-font-weight: normal">1-11</b> on electron impact leads to the elimination of H₂O from the molecular ions, albeit a minor process, resulting in the formation of 2-substituted-4(3<i style="mso-bidi-font-style:normal">H</i>)-quinazolinone radical cations. The mechanisms and ion-structure, proposed in the mass spectral study, are supported by high resolution data, Collision Activated Decomposition (CAD)-B/E-linked scan spectra and CAD MIKE spectrum. This mass spectrometry reaction has been fruitfully exploited in the laboratory to synthesise 4(3<i style="mso-bidi-font-style:normal">H</i>)-quinazolinones <b style="mso-bidi-font-weight:normal">13-23</b> in excellent yields by the pyrolysis of 2-(substituted benzamido)benzamides.</span></span>