33080-91-0Relevant academic research and scientific papers
The synthesis of 2-amino-4(3H)-quinazolinones and related heterocycles via a mild electrocyclization of aryl guanidines
Sales, Zachary S.,Mani, Neelakandha S.,Allison, Brett D.
supporting information, p. 1623 - 1626 (2018/03/29)
A new method for the preparation of 2-amino-4(3H)-quinazolinones and similar fused heterocycles is described. Simply warming a mixture of an aryl guanidine and carbonyl diimidazole in acetonitrile results in formation of a putative N-amidinoisocyanate intermediate which undergoes a 6π-electron electrocyclic reaction with the aryl ring to generate the quinazolinone ring system. The mild conditions are compatible with a variety of functional groups, and the reaction is shown to be successful on multigram scale.
One-Step Synthesis of 2-Chloropyrimidin-4-ol Derivatives: An Unusual Reactivity of Thiophosgene
Callingham, Michael,Blum, Francesca,Pavé, Grégoire
, p. 4930 - 4932 (2015/10/12)
A novel, high-yielding, one-step synthesis of 2-chloroquinazolin-4-ols and analogous bicycles from 2-aminoamides using thiophosgene is described. The scope of the reaction includes aminothioamides, amino acids, and fused heterocycle derivatives, furnishing quinazolines, oxazinones, and substituted fused pyrimidine bicycles, respectively. On the basis of observed results with substituted analogues, a mechanism for this transformation is thought to occur via an isothiocyanate intermediate followed by an unexpected chemoselective reaction of thiophosgene on the thiol intermediate.
Regioselective sulfonylation and N- to O-sulfonyl migration of quinazolin-4(3H)-ones and analogous thienopyrimidin-4(3H)-ones
Mertens, Matthias D.,Pietsch, Markus,Schnakenburg, Gregor,Guetschow, Michael
, p. 8966 - 8979 (2013/10/08)
The sulfonylation of quinazolin-4(3H)-ones and related tetrahydrobenzothieno[2,3-d]pyrimidin-4(3H)-ones with mesyl, tosyl, and p-cyanobenzenesulfonyl chloride was studied. A hydrogen substituent at 2-position directed the sulfonyl group to the N-3 position, while alkylsulfanyl or amino substituents led to sulfonylation of the carbonyl oxygen. The latter effect was attributed to steric influence and the positive mesomeric effect of the 2-substituent. An access to N-sulfonylated 2-substituted regioisomers was established. An unexpected 1,3-sulfonyl migration was observed and further analyzed. This process occurred as an intramolecular N- to O-shift as verified by kinetic and crossover experiments.
Efficient copper-catalyzed synthesis of 2-amino-4(3h)-quinazolinone and 2-aminoquinazoline derivatives
Huang, Xuhu,Yang, Haijun,Fu, Hua,Qiao, Renzhong,Zhao, Yufen
experimental part, p. 2679 - 2688 (2010/01/21)
We have developed a versatile and efficient method for copper-catalyzed synthesis of both 2-amino-4(3H)-quinazolinone and 2-aminoquinazoline derivatives. The protocol uses readily available substituted 2-halobenzoic acids, 2-bromobenzaldehyde, 2-bromophen
Synthesis of 4(3H)-Quinazolinones from Derivatives of Methyl 2-Isothiocyanatobenzoate
Dean, William D.,Papadopoulos, Eleftherios P.
, p. 1117 - 1124 (2007/10/02)
Ethyl N-((2-methoxycarbonylphenyl)thiocarbamate (2), N-(2-ethoxycarbonylphenyl)-4-methoxythiobenzamide (3b), and 2-(4-methoxyphenyl)4H,-3,1-benzothiazin-4-one (4a), react with nucleophilic reagents containing at least one primary amino group to yield a variety of 2-substituted and 2,4-disubstituted 4(3H)-quinazolinones, as well as some tricyclic and tetracyclic products.
