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Upstream product

• 4001-73-4 2-Bromobenzamide 
• 3218-36-8 4-Phenylbenzaldehyde 
• 3597-91-9 biphenyl-4-yl methanol 
• 28144-70-9 anthranilic acid amide 
• 119072-55-8 tert-butylisonitrile 
• 1591-31-7 4-iodo-biphenyl 
• 201230-82-2 carbon monoxide 
• 92-66-0 4-bromo-1,1'-biphenyl 
• 1885-29-6 anthranilic acid nitrile 
• 712-76-5 N-(4-phenyl)benzylamine 
• 2350-89-2 p-vinylbiphenyl 
• 118-48-9 isatoic anhydride 

Relevant academic research and scientific papers

N^N^O hydrazone capped pincer type palladium complex catalysed construction of quinazolinones from alcohols

New Pincer type Pd(II) complex [Pd(NNO)(PPh3)] (1) prompted synthesis of quinazolinones via dehydrogenative coupling of readily accessible alcohols, and o-aminobenzamide is described. A diverse range of quinazolinones has been synthesized efficiently with good to excellent yields employing low catalyst loading (0.5 mol%) under the aerobic condition without any additives/oxidants. A plausible mechanism for the construction of quinazolinones has been proposed via cyclic aminal intermediate. Large-scale synthesis attests to the productiveness of the current strategy.

Palladium(II) N^O Chelating Complexes Catalyzed One-Pot Approach for Synthesis of Quinazolin-4(3 H)-ones via Acceptorless Dehydrogenative Coupling of Benzyl Alcohols and 2-Aminobenzamide

A convenient protocol for the one-pot synthesis of quinazolin-4(3H)-ones using palladium(II) complexes via dehydrogenative coupling of readily available benzyl alcohols and 2-aminobenzamide has been described. New structurally related Pd(II) N^O chelating complexes of general configuration [Pd(L)Cl(PPh3)] (where L = dimethylamino benzoylhydrazone ligands) have been designed and synthesized. The formation of the complexes has been recognized by analytical and spectral methods (FT-IR, NMR, HR-MS). The presence of a square-planar geometry around the palladium(II) ion was confirmed by single crystal X-ray diffraction study. A wide range of substituted quinazolinones have been successfully achieved from a diverse range of benzyl alcohols in good to excellent yields using 1.0 mol % of catalyst loading under aerobic conditions. Furthermore, control experiments reveal that the dehydrogenative coupling reaction involves initially the formation of an aldehyde intermediate and subsequent formation of a cyclic aminal intermediate.

Photocatalyst-free visible-light-promoted quinazolinone synthesis at room temperature utilizing aldehydes generatedin situ viaC=C bond cleavage

This is the first report on a facile tandem route for synthesizing quinazolinones at room temperature from various aminobenzamides andin situ-generated aldehydes. The latter was formedviaC=C bond cleavage, and the overall reaction proceeded using molecular oxygen as a clean oxidant in the absence of a photocatalyst. Visible light, which was indispensable for the entire course of the reaction, played multiple roles. It initially cleaved styrene to an aldehyde, then facilitated its cyclization with ano-substituted aniline, and finally promoted the dehydrogenation of the cyclized intermediate. The previous step provided the feedstock for the next step in the reaction, thereby preventing volatilization, oxidation, and polymerization of the aldehyde. Thus, the overall process is simple, environmentally benign, and economically feasible.

Aerobic primary and secondary amine oxidation cascade by a copper amine oxidase inspired catalyst

Herein, we report a bioinspired catalytic system for the one-pot cascade oxidation of a native primary amine and anin situgenerated non-native secondary amine. The catalyst consists of ano-quinone cofactor phd (1,10-phenanthroline-5,6-dione) and a copper ion and operates under ambient air conditions. Quinazolin-4(3H)-ones, which are common pharmacophores present in numerous pharmaceuticals and bioactive compounds, were synthesized in high yields. A detailed kinetic and mechanistic study elucidates the role of the catalyst in the multi-step oxidative cascade reaction.

Discovery of Quinazolin-4(3 H)-ones as NLRP3 Inflammasome Inhibitors: Computational Design, Metal-Free Synthesis, and in Vitro Biological Evaluation

NLRP3 inflammasome is an important therapeutic target for a number of human diseases. Herein, computationally designed series of quinazolin-4(3H)-ones were synthesized using iodine-catalyzed coupling of arylalkynes (or styrenes) with O-aminobenzamides. The key event in this transformation involves the oxidative cleavage of the C-C triple/double bond and the release of formaldehyde. The reaction relies on the C-N bond formation along with the C-C bond cleavage under metal-free conditions. The nitro-substituted quinazolin-4(3H)-one 2k inhibited NLRP3 inflammasome (IC50 5 μM) via the suppression of IL-1β release from ATP-stimulated J774A.1 cells.

Chemoselective Trifluoroethylation Reactions of Quinazolinones and Identification of Photostability

Herein, we report chemoselective trifluoroethylation routes of unmasked 2-arylquinazolin-4(3H)-ones using mesityl(2,2,2-trifluoroethyl)iodonium triflate at room temperature. Homologous C-, O-, and N-functionalized subclasses are accessed in a straightforward manner with a wide substrate scope. These chemoselective branching events are driven by Pd-catalyzed ortho-selective C-H activation at the pendant aryl ring and base-promoted reactivity modulation of the amide group, leveraging the intrinsic directing capability and competing pronucleophilicity of the quinazolin-4(3H)-one framework. Furthermore, outstanding photostability of the quinazolin-4(3H)-one family associated with nonradiative decay is presented.

Synthesis and structure–activity relationship study of novel quinazolinone-based inhibitors of MurA

MurA is an intracellular bacterial enzyme that is essential for peptidoglycan biosynthesis, and is therefore an important target for antibacterial drug discovery. We report the synthesis, in silico studies and extensive structure–activity relationships of a series of quinazolinone-based inhibitors of MurA from Escherichia coli. 3-Benzyloxyphenylquinazolinones showed promising inhibitory potencies against MurA, in the low micromolar range, with an IC50 of 8?μM for the most potent derivative (58). Furthermore, furan-substituted quinazolinones (38, 46) showed promising antibacterial activities, with MICs from 1?μg/mL to 8?μg/mL, concomitant with their MurA inhibitory potencies. These data represent an important step towards the development of novel antimicrobial agents to combat increasing bacterial resistance.

Bimetallic Cu–Mn-Catalyzed Synthesis of 2-Arylquinazolin-4(3H)-ones: Aqueous Ammonia as Source of a Ring Nitrogen Atom

A new method for the synthesis of 2-arylquinazolin-4(3H)-ones that involves a three-component coupling reaction of 2-bromobenzamide, aryl aldehydes, and aqueous ammonia has been developed. This protocol employs Cu–Mn spinel oxide as a heterogeneous catalyst and does not require the presence of a ligand or external oxidant. Key features of the reaction include a recyclable catalyst, ligand-free conditions, and a wide scope of possible substrates. The mechanism begins with the replacement of the bromine atom with NH2from aqueous ammonia followed by imine formation, intramolecular ring cyclization (C–N bond formation), and aromatization.

A catalyst-free rapid, practical and general synthesis of 2-substituted quinazolin-4(3H)-ones leading to luotonin B and E, bouchardatine and 8-norrutaecarpine

A remarkably rapid but microwave/ultrasound/catalyst-free method has been developed for the construction of a quinazolin-4(3H)-one ring using formamide as an efficient ammonia precursor and PEG-400 as an effective solvent. The methodology afforded various 2-substituted quinazolin-4(3H)-one derivatives in good yield via a three-component reaction of isatoic anhydride, aldehydes and formamide in air. This single methodology was extended successfully to the synthesis of several alkaloids e.g. leutonin B and E, bouchardatine and 8-norrutaecarpine.

Solid-phase synthesis of benzazoles, quinazolines, and quinazolinones using an alkoxyamine linker

An alkoxyamine linker was applied for the solid-phase synthesis of benzazoles, quinazolines, and quinazolinones. Aromatic aldehydes were anchored by aldoxime linkage. After some reactions on a solid support, the products were cleaved with paraformaldehyde under the acidic conditions to afford the corresponding aldehydes, which were subsequently subjected to oxidative coupling with 2-substituted anilines under air atmosphere to give the desired compounds.