3525-01-7Relevant academic research and scientific papers
Facile synthetic route to benzo[c]chromenones and thieno[2,3-c]chromenones
Shyyka, Olga Ya.,Martyak, Roman L.,Tupychak, Mykola A.,Pokhodylo, Nazariy T.,Obushak, Mykola D.
, p. 2399 - 2405 (2017)
Convenient two-step procedure for the synthesis of fused chromenone derivatives was developed. Reduction of the obtained in the Meerwein arylation reaction aryl- and thienylquinones allowed to construct 6H-benzo[c]chromene-6-ones and 4H-thieno[2,3-c]chrom
Rh(III)-Catalyzed sequential: Ortho-C-H oxidative arylation/cyclization of sulfoxonium ylides with quinones toward 2-hydroxy-dibenzo [b,d] pyran-6-ones
Cheng, Jiang,Dong, Yaqun,Sun, Song,Yu, Jin-Tao
, p. 6688 - 6691 (2020)
A rhodium(iii)-catalyzed ortho-C-H functionalization of sulfoxonium ylides followed by intramolecular annulation reactions with quinones was described, where the carbonyl in sulfoxonium ylides served as a chelation group. This protocol leads to the effici
Kinetic Control of Rh(III)-Catalyzed Annulation of C-H Bonds with Quinones: Chemoselective Synthesis of Hydrophenanthridinones and Phenanthridinones
Yang, Wei,Wang, Jingyi,Wei, Zhonglin,Zhang, Qian,Xu, Xianxiu
, p. 1675 - 1680 (2016)
A temperature-dependent redox-neutral Rh(III)-catalyzed C-H bond annulation of N-methoxybenzamides with quinones was developed for the chemoselective synthesis of hydrophenanthridinones and phenanthridinones. This reaction involves an Rh(III)-catalyzed C-H bond functionalization and a subsequent cyclization through the directing group nucleophilic addition to the carbonyl group at room temperature. (Figure Presented).
C-H bond functionalization of benzoic acid: Catalytic synthesis of 2-hydroxy-6 H -benzo[c]chromen-6-ones using (Cp*IrCl2) 2
Engelman, Kristi L.,Feng, Yuee,Ison, Elon A.
, p. 4572 - 4577 (2011)
Catalytic H/D exchange reactions of benzene and benzoic acid with deuterated solvents have been studied using (Cp*IrCl2) 2. A 1:1 mixture of D2O/CD3OD produced the highest turnover numbers for benzene. High levels of deuterium incorporation into benzoic acid were observed only when sodium acetate was added to the reaction mixture. Attempts at producing hydroxybenzoic acid by catalytic C-H functionalization of benzoic acid with benzoquinone were unsuccessful. Instead, 2-hydroxy-6H-benzo[c]chromen-6-one was isolated as the major product. An array of substituted benzoic acids was analyzed for this functionalization reaction. Preliminary mechanistic studies indicate that the benzochromenones are formed by C-H bond activation of benzoic acid followed by insertion of benzoquinone into the iridium-carbon bond.
Rh(III)-catalyzed C-H activation of benzamides: Coupling with quinones
Qi, Zisong,Li, Xingwei
, p. 48 - 56 (2015)
Rh(III)-catalyzed C-H activation of N-(alkyl)benzamides in the oxidative coupling with various quinones. In addition, under redox-neutral conditions, 2-hydroxy-6H-benzo[c]chromen-6-ones were also obtained via a cascade of cross-coupling followed by lactonization.
Synthesis of Polycyclic Cyclohexadienone through Alkoxy-Oxylactonization and Dearomatization of 3′-Hydroxy-[1,1′-biphenyl]-2-carboxylic Acids Promoted by Hypervalent Iodine
Deng, Qingfu,Hu, Wen,Hussain, Muhammad Ijaz,Xia, Wen,Xiong, Yan,Zhang, Xiaohui
, p. 3125 - 3133 (2020/03/23)
Alkox-oxylactonization and dearomatization of 3′-hydroxy-[1,1′-biphenyl]-2-carboxylic acid simultaneously promoted by hypervalent iodine have been developed using stoichiometric PhI(OAc)2 or a catalytic amount of chiral aryl-λ3-iodane generated in situ. This reaction provides a concise method to synthesize diverse polycyclic cyclohexadienones as potential inhibitors of DNA polymerase under mild reaction conditions.
Rh(iii)-catalyzed oxidative C-H bond arylation with hydroquinones: Sustainable synthesis of dibenzo[b,d]pyran-6-ones and benzo[d]naphtho[1,2-b]pyran-6-ones
Yang, Wei,Wang, Shan,Zhang, Qian,Liu, Qun,Xu, Xianxiu
supporting information, p. 661 - 664 (2015/01/16)
An efficient Rh(iii)-catalyzed C-H bond arylation with phenol derivatives was developed for the direct and sustainable synthesis of dibenzo[b,d]pyran-6-ones and benzo[d]naphtho[1,2-b]pyran-6-ones. This reaction shows good substrate scope and excellent fun
Derivatization of coumarins at the benzenoid ring in aqueous medium
Bhunia, Sankar C.,Pal, Sutanuka,Patra, Gopal C.,Pal, Sudhir C.
, p. 1679 - 1688 (2015/02/02)
Some 6-disubstituted, 8-disubstituted, and/6,8-disubstituted compounds have been prepared from coumarin, 7-methylcoumarin, and 3,4-benzocoumarin. The Reimer-Tiemann reaction, Lederer-Manasse reaction, bromination using molecular bromine as well as 2,4,4,6-tetrabromocyclohex-2,5-dien-1-one, Elbs reaction, and diazocoupling have been carried under controlled conditions to obtain various derivatives. Further, several reactions of aldehyde derivatives of these coumarins have been carried on to prepare important functional compounds including some heterocycles. It is noteworthy that these aldehydes behave as phenolic aldehydes under alkaline conditions to undergo the Dakin reaction. The reactions are mostly carried in aqueous media involving a dianionic intermediate and hence fulfill one important criterion of green chemistry.
Synthesis of 6H-Dibenzopyran-6-ones via Dienone-Phenol Rearrangements of Spiro-3'-ones
Hart, David J.,Kim, Adrienne,Krishnamurthy, Ramanarayanan,Merriman, Gregory H.,Waltos, Anne-Marie
, p. 8179 - 8188 (2007/10/02)
A series of spiro-3'-ones were prepared from metallated benzamides and 4,4-dimethoxycyclohexadienone.Rearrangement of these spirodienones under a variety of conditions gave substituted 6H-dibenzopyran-6-ones.Rearrangements in aqueous sulfuric acid gave products of formal O-migration while rearrangements in trifluoroacetic anhydride-trifluoroacetic acid-sulfuric acid usually gave C-migration products.Key Words: dienone-phenol rearrangement; 6H-dibenzopyran-6-one, spiro-3'-one
