86672-48-2Relevant articles and documents
Remarkable conversion of 2-thioxo-2,3-dihydroquinazolin-4(1H)-ones into the corresponding quinazoline-2,4(1H,3H)-diones: Spectroscopic analysis and X-ray crystallography
El-Azab, Adel S.,Khalil, Nasr Y.,Abdel-Aziz, Alaa A.-M.
, (2021/04/26)
A simple and efficient new synthetic method to obtain 3-substituted quinazolin-2,4-diones 9.16 by the reaction of 3-substituted 2- thioxo-quinazolin-4-ones 1.8 with sodamide under mild conditions was presented. The structure of the newly synthesized compounds was determined by infrared spectroscopy, UV-visible spectroscopy, nuclear magnetic resonance, and single-crystal X-ray crystallographic analysis. The crystal structure of 6-methyl-3-phenylquinazoline-2,4(1H,3H)-dione (11) [C15H12N2O2: MF. 252.27, triclinic, P-1, a = 7.8495 (13) ?, b= 12.456 (2) ?, c = 13.350 (2) ?, α = 103.322 (3)°, β = 90.002 (3)°, γ = 102.671 (4)°, V. 1237.5 (3) ?3, Z= 4, R = 0.0592, wR= 0.1699, S= 1.039] was determined. In the crystal cell, two identical conformers of compound 11 were found connected by intramolecular hydrogen bonds, responsible for the favourable occurrence of these two independent molecules.
Palladium-Catalyzed Cyclocarbonylation of o-Iodoanilines with Heterocumulenes: Regioselective Preparation of 4(3H)-Quinazolinone Derivatives
Larksarp, Chitchamai,Alper, Howard
, p. 2773 - 2777 (2007/10/03)
A catalyst system comprising palladium acetate - bidentate phosphine is effective for the cyclocarbonylation of o-iodoanilines with heterocumulenes at 70-100°C for 12-24 h to give the corresponding 4(3H)-quinazolinone derivatives in good yields. Utilizing o-iodoaniline with isocyanates, carbodiimides, and ketenimines for the reaction, 2,4-(1H,3H)-quinazolinediones, 2-amino-4(3H)-quinazolinones and 2-alkyl-4(3H)-quinazolinones were obtained, respectively. The nature of the substrates including the electrophilicity of the carbon center of the carbodiimide, and the stability of the ketenimine, influence the product yields of this reaction. Urea-type intermediates are believed to be generated first in situ from the reaction of o-iodoanilines with heterocumulenes, followed by palladium-catalyzed carbonylation and cyclization to yield the products.