Short Note
Version 1
Preserved in Portico This version is not peer-reviewed
3a-(4-Chlorophenyl)-1-thioxo-2,3,3a,4-tetrahydroimidazo[1,5-a]quinazolin-5(1H)-one
Version 1
: Received: 21 June 2024 / Approved: 22 June 2024 / Online: 24 June 2024 (10:13:03 CEST)
A peer-reviewed article of this Preprint also exists.
Defant, A.; Innocenti, N.; Mancini, I. 3a-(4-Chlorophenyl)-1-thioxo-2,3,3a,4-tetrahydroimidazo[1,5-a]quinazolin-5(1H)-one. Molbank 2024, 2024, M1859. Defant, A.; Innocenti, N.; Mancini, I. 3a-(4-Chlorophenyl)-1-thioxo-2,3,3a,4-tetrahydroimidazo[1,5-a]quinazolin-5(1H)-one. Molbank 2024, 2024, M1859.
Abstract
With the aim to produce new heterocycle molecules, the previously reported 2-(aminomethyl)-2-(4-chlorophenyl)-2,3-dihydroquinazolin-4(1H)-one was converted efficiently by reacting with N,N’-dithiocarbonyldiimidazole (DTCI), to produce the substituted imidazolidine-2-thione moiety inserted in a three fused ring scaffold of the title compound. The molecular composition was confirmed by a high-resolution MS experiment, and its structure was elucidated by 1H, 13CNMR, and IR analyses. The thioacetamide form of the product was supported by density functional theory (DFT)-NMR analysis where 13C chemical shifts of thioacetamide form and of its iminothiol tautomer were calculated in chloroform at the BP86 /Jgauss-TZP2 level of theory. The very good linear correlation between 13C chemical shifts by experiment and by calculation for the NHC=S form confirmed the structure.
Keywords
substituted imidalidine-2-thione; heterocycles synthesis; NMR analysis; density functional theory (DFT); tautomerism.
Subject
Chemistry and Materials Science, Organic Chemistry
Copyright: This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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