18287-99-5

Upstream product

• 98-86-2 acetophenone 
• 1761-61-1 5-bromosalicyclaldehyde 

Downstream Products

• 1218-80-0 6-bromoflavone 
• 1429326-80-6 (6S,12S)-2-bromo-6-phenyl-6,12-methano-12H-dibenzo[d,g][1,3]dioxocin 
• 89406-24-6 4-Bromo-2-(4-phenyl-2,3-dihydro-benzo[b][1,4]thiazepin-2-yl)-phenol 
• 1602919-17-4 (2R,3S,4S)-1'-tert-butyl 2-ethyl 6-bromo-2'-oxo-4-(2-oxo-2-phenylethyl)spiro[chroman-3,3'-indoline]-1',2-dicarboxylate 
• 1589534-72-4 C₂₃H₁₇BrO₃ 
• 1589534-43-9 6-bromo-1,3-diphenylbenzofuro[2,3-c]pyridine 
• 1450898-83-5 (E)-3-[2-(2-oxopropoxy)-5-bromophenyl]-1-phenylprop-2-en-1-one 

Relevant academic research and scientific papers

Synthesis of (Het)aryl 2-(2-hydroxyaryl)cyclopropyl ketones

A simple general method for the synthesis of 1-acyl-2-(ortho-hydroxyaryl)cyclopropanes, which belong to the donor–acceptor cyclopropane family, has been developed. This method, based on the Corey–Chaykovsky cyclopropanation of 2-hydroxychalcones, allows f

Palladium-Catalyzed Cascade Reactions of 2-(Cyanomethoxy)chalcones with Arylboronic Acids: Selective Synthesis of Emissive Benzofuro[2,3- c]pyridines

The Pd(II)-catalyzed cascade reactions of 2-(cyanomethoxy)chalcones with arylboronic acids were demonstrated, allowing the rapid construction of benzofuro[2,3-c]pyridine skeletons with excellent selectivity. These transformations involve the domino-style formation of C-C/C-C/C-N bonds through nitrile carbopalladation, intramolecular Michael addition, cyclization, and aromatization. This chemistry allows for the reactions of 2-(cyanomethoxy)chalcones with thiophen-3-ylboronic acid, providing 3-aryl-1-(thiophen-3-yl)benzofuro[2,3-c]pyridines in moderate to good yields. In addition, the resulting products represent a new class of emissive fluorophores.

MANGANESE (III) CATALYZED C--H AMINATIONS

Reactions that directly install nitrogen into C—H bonds of complex molecules are significant because of their potential to change the chemical and biological properties of a given compound. Selective intramolecular C—H amination reactions that achieve high levels of reactivity, while maintaining excellent site-selectivity and functional-group tolerance is a challenging problem. Herein is reported a manganese perchlorophthalocyanine catalyst [MnIII(ClPc)] for intermolecular benzylic C—H amination of bioactive molecules and natural products that proceeds with unprecedented levels of reactivity and site-selectivity. In the presence of Br?nsted or Lewis acid, the [MnIII(ClPc)]-catalyzed C—H amination demonstrates unique tolerance for tertiary amine, pyridine and benzimidazole functionalities. Mechanistic studies indicate that C—H amination proceeds through an electrophilic metallonitrene intermediate via a stepwise pathway where C—H cleavage is the rate-determining step of the reaction. Collectively these mechanistic features contrast previous base-metal catalyzed C—H aminations.

Synthesis and antimicrobial activity of some 5-chloro-3-phenyl-1H-indole-2-carbonyl azide derivatives

In the present investigations, a series of new 6-substituted-3-(5-chloro-3-phenyl-lJ?-indole-2yl)-3,4-dihydro-4-substituted-4-substituted-phenacyl-2H-l,3-benzoxazin-2-one 7a-f have been synthesized by two methods making use of 5-chloro-3-phenyl-l/H-ndole-2-carbonyl azide 2 and chalcones 5a-f. In one method, compound 2 on reaction with chalcones 5a-f in presence of triethylamine in dry benzene yields respective open chain carbamates 6a-f, followed by reaction with catalytic amount of potassium hydroxide in dry benzene under reflux condition to afford compounds 7a-f. In another method, compound 5a-f on reaction with compound 2 using dry benzene in presence of catalytic amount of potassium hydroxide under reflux conditions afford cyclized products 7a-f in good yield. Structures of the all the newly synthesized compounds have been confirmed by spectral data. All these compounds have been screened for their antibacterial activity against Staphylococcus aureus, Escherichia coli, Bacillus subtilis, antifungal activity against Aspergillus Niger and Candida albicans and antituberculosis activity against Mycobacterium tuberculosis (H37RV).

Exploitation of new chalcones and 4H-chromenes as agents for cancer treatment

Chalcone and chromene derivatives were synthesized in good yield through simple and effective reactions using innocuous solvents such as water and ethanol and high yielding aldol condensations. Generally, the reactions were performed at room temperature, leading to the isolation of highly pure compounds. These compounds were tested on breast cancer cells (MCF-7 and Hs578T) and breast non-neoplastic cells (MCF-10A). After determination of IC50 value, specific assays were performed to analyze the potential of these compounds, and those bearing halogenated substituents presented enhanced activity comparing to methoxyl or methyl groups. More specifically, the bromine atom was often present in the bioactive molecules that proceeded to the final assays and showed to be promising candidates for further studies. The selected chromene acted as a cell migration inhibitory agent and triggered regulated cell death associated with G2/M cell-arrest and microtubule destabilization. For chalcones, the results suggest an anti-proliferative activity. Also, results for combination-therapy potentiated the antitumor effect of doxorubicin and reduced cytotoxicity in MCF-10A cells.

Facile synthesis of 4H-chromene derivatives via base-mediated annulation of orffro-hydroxychalcones and 2-bromoallyl sulfones

The cesium carbonate-mediated reaction of 2-bromoallyl sulfones and ortho-hydroxychalcones furnished 3-arylsulfonyl-4H-chromene derivatives in 58-67% yield (18 examples). 2-Bromoallyl sulfones functioned as synthetic surrogates for allenyl sulfones in the reaction.

Enantioselective Synthesis of Highly Substituted Chromans via the Oxa-Michael-Michael Cascade Reaction with a Bifunctional Organocatalyst

A highly enantioselective synthesis of chiral chroman derivatives via an oxa-Michael-Michael cascade reaction has been developed using a bifunctional thiourea organocatalyst. The products were obtained with excellent enantioselectivities (up to >99%), good yields (up to 95%), and diastereoselectivities (up to 5:1).

Intramolecular oxidative coupling: I2/TBHP/NaN3-mediated synthesis of benzofuran derivatives

A novel intramolecular oxidative coupling reaction has been established to prepare benzofuran derivatives via direct C(sp2)-H functionalization for the formation of C-O bond. This transformation is mediated by I2/TBHP/NaN3 under metal-free conditions and a catalytic amount of NaN3 plays a crucial role in the reaction. Furthermore, the reaction tolerates a broad substrate scope with average to excellent yields.

ZrCl4-catalysed synthesis of new 4-(2-hydroxyphenyl)pyrazolo[3,4-b]pyridine derivatives

In the presence of a catalytic amount of zirconium(IV) chloride, an efficient synthesis of new 4-(2-hydroxyphenyl)pyrazolo[3,4-b]pyridines has been developed by the reaction 2-hydroxychalcones with 3-methyl-1-phenyl-1H-pyrazol-5-amine in refluxing ethanol. All these novel compounds have been characterised by 1H NMR, 13C NMR, HRMS, IR spectra and X-ray crystallographic analysis.

An advanced and novel one-pot synthetic method for diverse benzo[c]chromen-6-ones by transition-metal free mild base-promoted domino reactions of substituted 2-hydroxychalcones with β-ketoesters and its application to polysubstituted terphenyls

Novel and efficient one-pot syntheses of a variety of benzo[c]chromen-6-one derivatives were accomplished using Cs2CO3-promoted reactions between substituted 2-hydroxychalcones and β-ketoesters. These reactions involved domino Michael addition/intramolecular aldol/oxidative aromatization/lactonization and provided a rapid synthetic route for the production of biologically interesting novel benzo[c]chromen-6-one molecules bearing several different substituents on benzene rings. As an application of this methodology, several synthesized benzo[c]chromen-6-ones were transformed into highly functionalized novel terphenyls.