A Novel Highly Stereoselective Synthesis of 2,3‐Disubstituted 3H‐Quinazoline‐4‐one Derivatives.

Zhichkin, Paul E.; Kesicki, Edward A.; Treiberg, Jennifer; Bourdon, Lisa H.; Ronsheim, Matthew D.; Ooi, Hua Chee; White, Stephen; Judkins, Angela; Fairfax, David J.

doi:10.1002/chin.200733147

Cited by 2 publications

(2 citation statements)

References 2 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Therefore, the development of the efficient synthetic methods for various quinazolinones has attracted great interest from synthetic chemistry. Most of the reported methods are about the synthesis of quinazoline-4-ones [10][11][12][13][14][15] and quinazoline-2,4-(1H,3H)-diones. [16][17][18][19] Only a two-step reaction has been reported for the synthesis of quinazoline-5-ones 8 although octahydroquinazoline-5-ones, for example III in 3…”

Section: Introductionmentioning

confidence: 99%

Efficient Synthesis of a Series of Novel Octahydroquinazoline-5-ones via a Simple on-Water Urea-Catalyzed Chemoselective Five-Component Reaction

et al. 2016

View full text Add to dashboard Cite

Multicomponent reactions (MCRs) have become a powerful tool for drug discovery and development owing to their advantages of fast and efficient construction of a large library of products with complexity and diversity. However, conventional MCRs usually proceed in environmentally unfriendly organic solvents rather than in water, a green solvent used by nature for biological chemistry. Herein, a simple and efficient on-water urea-catalyzed chemoselective five-component reaction (5CR) has been developed for the synthesis of a series of novel octahydroquinazoline-5-ones (6), the derivatives of quinazolinones possessing diverse biological activities. The molecular structure of 6{1,1,12} has been confirmed by single-crystal X-ray diffraction. The 5CR can proceed at room temperature under normal atmospheric pressure in good yields and afford a large library of octahydroquinazoline-5-ones with various aromatic and aliphatic substituents at N-1, C-2, and N-3. In addition, a green method has been developed for the synthesis of enaminones, important intermediates in the 5CR and in synthetic chemistry.

show abstract

Section: Introductionmentioning

confidence: 99%

Efficient Synthesis of a Series of Novel Octahydroquinazoline-5-ones via a Simple on-Water Urea-Catalyzed Chemoselective Five-Component Reaction

et al. 2016

View full text Add to dashboard Cite

show abstract

“…19,20 The benzamide moiety is found in a wide range of biologically active molecules and substituted benzamides have been used as insecticides, antiviral, and anti-inflammatory agents. [21][22][23][24][25] These compounds with variability in conformation are influenced by both electronic and structural effects. 26,27 A systematic study on halogen substituted benzamide has revealed that strong N-H• • •O=C interactions largely remain preserved in…”

Section: Introductionmentioning

confidence: 99%

Quantitative investigation of intermolecular interactions in dimorphs of 3-Chloro-N-(2-fluorophenyl)benzamide and 2-Iodo-N-(4- bromophenyl)benzamide

et al. 2018

View full text Add to dashboard Cite

In this study, we have analyzed the role of different intermolecular interactions in the polymorphic modifications of 3-chloro-N-(2-fluorophenyl)benzamide (I) and 2-iodo-N-(4-bromophenyl)benzamide (II). The crystals were obtained via slow evaporation method with the alteration of solvents for crystallization. The already reported form [Cryst. Growth Des. (2011) 11:1578] crystallizes in P2 1 /c with Z =2 [Form IA], while the new form crystallizes in Pna2 1 with Z =1 [Form IB]. The latter compound crystallizes in P2 1 /n with Z =1 [Form IIA] and in Pbca with Z =1 [Form IIB]. Weak Cl• • •Cl and C-H• • •F interactions in the former (IA, IB) and weak I• • •I and C-H• • • π interactions in the latter (IIA, IIB) play a vital role in the formation of different polymorphic modifications leading to the observation of conformational and packing polymorphs, respectively. PIXEL calculations show that most of the interactions present in the crystal structures are dispersive in nature. 2D Fingerprint plots revealed that the relative contribution of different intermolecular interactions in different polymorphic forms was different.

show abstract

A Novel Highly Stereoselective Synthesis of 2,3‐Disubstituted 3H‐Quinazoline‐4‐one Derivatives.

Cited by 2 publications

References 2 publications

Efficient Synthesis of a Series of Novel Octahydroquinazoline-5-ones via a Simple on-Water Urea-Catalyzed Chemoselective Five-Component Reaction

Efficient Synthesis of a Series of Novel Octahydroquinazoline-5-ones via a Simple on-Water Urea-Catalyzed Chemoselective Five-Component Reaction

Quantitative investigation of intermolecular interactions in dimorphs of 3-Chloro-N-(2-fluorophenyl)benzamide and 2-Iodo-N-(4- bromophenyl)benzamide

Contact Info

Product

Resources

About