32212-33-2Relevant academic research and scientific papers
Observation of a Tetrahedral Intermediate and Its Anion in a Hydrolysis Reactions. Ring Opening of a Quinazolinium Ion
Tee, Oswald S.,Trani, Michael,McClelland, Robert A.,Seaman, N. Esther
, p. 7219 - 7224 (1982)
The behavior of the 3,4-dihydro-1,3-dimethyl-4-oxoquinazolinium ion (Q+) in basic aqueous solution (pH 7-14) has been studied.Kinetic studies afforded information about four distinct processes: (a) the relatively fast equilibration of Q+/
Electrochemical utilization of methanol and methanol-d4 as a C1 source to access (deuterated) 2,3-dihydroquinazolin-4(1H)-one
Liu, Mingzhu,Wei, Yu,Xu, Liang
supporting information, (2021/10/06)
Herein, an electrocatalytic protocol for the synthesis of 2,3-dihydroquinazolin-4(1H)-one has been disclosed. Methanol is activated and utilized as the C1 source to cyclize with 2-aminobenzamides. This cyclization reaction proceeds conveniently (room temperature and air atmosphere) without any homogeneous metal catalysts, external oxidants, or bases. A wide variety of N,N-disubstituted 2,3-dihydroquinazolin-4(1H)-ones are obtained via this approach. Moreover, when methanol-d4 is used, a deuterated methylene motif is incorporated into the N-heterocycles, providing an efficient approach to the deuterated N-heterocycles.
Experimental and theoretical investigations into the stability of cyclic aminals
Sawatzky, Edgar,Drakopoulos, Antonios,R?lz, Martin,Sotriffer, Christoph,Engels, Bernd,Decker, Michael
supporting information, p. 2280 - 2292 (2016/11/17)
Background: Cyclic aminals are core features of natural products, drug molecules and important synthetic intermediates. Despite their relevance, systematic investigations into their stability towards hydrolysis depending on the pH value are lacking. Results: A set of cyclic aminals was synthesized and their stability quantified by kinetic measurements. Steric and electronic effects were investigated by choosing appropriate groups. Both molecular mechanics (MM) and density functional theory (DFT) based studies were applied to support and explain the results obtained. Rapid decomposition is observed in acidic aqueous media for all cyclic aminals which occurs as a reversible reaction. Electronic effects do not seem relevant with regard to stability, but the magnitude of the conformational energy of the ring system and pKa values of the N-3 nitrogen atom. Conclusion: Cyclic aminals are stable compounds when not exposed to acidic media and their stability is mainly dependent on the conformational energy of the ring system. Therefore, for the preparation and work-up of these valuable synthetic intermediates and natural products, appropriate conditions have to be chosen and for application as drug molecules their sensitivity towards hydrolysis has to be taken into account.
Studies of the H-D exchange mechanism of malonganenone B
Clark, Peter G. K.,Lein, Matthias,Keyzers, Robert A.
supporting information; experimental part, p. 1725 - 1729 (2012/04/11)
Malonganenone B (1) exhibits an unusual H-D exchange of a formyl proton when in deuteric-NMR solvents. Synthetic and kinetic investigations were made to probe the mechanism of this exchange, which appears to occur via an uncommon and transient amine-amide
COMPOUNDS THAT MODULATE EGFR ACTIVITY AND METHODS FOR TREATING OR PREVENTING CONDITIONS THEREWITH
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Page/Page column 86-87, (2011/11/30)
Provided are compounds and methods for treating or preventing kinase-mediated disorders therewith.
2,1-Benzisothiazoles. XIII . Intermediates and Products in the Sulfur Extrusion Reaction of 2,1-Benzisothiazolines-3(1H)-one. A New Synthesis of 11H-Pyridoquinazolin-11-one ("Pyracridone")
Davis, Michael,Hook, Robert J.,Wu, Wen Yang
, p. 369 - 373 (2007/10/02)
Triethyl phosphite abstracts sulfur from 2,1-benzisothiazolin-3(1H)-one (1); a reaction intermediate is the spirocyclic compound 11, and products include the benzoxazine 6 and polyanthraniloyl compounds.In the presence of pyridine, pyracridone (13) is formed.The ketene-imine 9 is probably not an intermediate in these reactions.The reactions of other nucleophiles with 1 and with its N-methyl derivative 15, have been examined.
