An organophosphorus-mediated cross-Rauhut-Currier/Wittig domino reaction for the efficient synthesis of trisubstituted cyclopentenes.

An efficient organophosphorus-mediated cross-Rauhut-Currier/Wittig domino reaction of vinyl ketones with chalcones has been developed for the synthesis of trisubstituted cyclopentenes. The new synthetic method has the advantages of mild reaction conditions, high efficiency, environmental friendliness and satisfactory yields.

The BRD4 inhibitor JQ1 protects against chronic obstructive pulmonary disease in mice by suppressing NF-κB activation.

Objective: To examine the effect of the BRD4 inhibitor JQ1 on mice with chronic obstructive pulmonary disease (COPD) via NF-κB.

Methods: COPD models constructed by exposure to cigarette smoke and intratracheal instillation of lipopolysaccharides (LPS) in mice were treated with JQ1 (15, 25 or 50 mg/kg). HE staining was performed to observe histopathological changes in the lung tissues.

Association between Interleukin-10 Gene Polymorphisms and Behcet's Disease Susceptibility: Evidence from a Meta-Analysis.

Epidemiological studies have demonstrated that interleukin-10 (IL-10) polymorphisms may be associated with the development of Behcet's disease (BD). However, the published results were inconsistent. Therefore, this meta-analysis was conducted to derive a more precise relationship between IL-10 polymorphisms and BD susceptibility.

A Cascade Dehydrogenative Cross-Coupling/Annulation Reaction of Benzamides with β-Keto Esters for the Synthesis of Isoquinolinone Derivatives.

A novel cascade DCC/annulation reaction of N-alkoxybenzamides with β-keto esters has been developed for the synthesis of isoquinolinone derivatives under palladium catalysis. A plausible mechanism involving α-C(sp)-H activation and a Pd(II)/Pd(IV) catalytic cycle is also proposed.

A cascade C-H functionalization/cyclization reaction of N-arylpyridin-2-amines with α,β-unsaturated aldehydes for the synthesis of dihydroquinolinone derivatives under rhodium catalysis.

A novel cascade C-H functionalization/cyclization reaction of N-arylpyridin-2-amines with α,β-unsaturated aldehydes has been developed under rhodium catalysis, affording dihydroquinolinone derivatives in moderate to excellent yields. A plausible mechanism of dual catalytic cycles by rhodium(iii) catalysis is also proposed.

A Four-Component Cascade C-H Functionalization/Cyclization/Nucleophilic Substitution Reaction To Construct α-Functionalized Tetrahydroquinolines by the Strategy of in Situ Directing Group Formation.

A four-component cascade C-H functionalization/cyclization/nucleophilic substitution reactions of anilines, carboxylic anhydrides, propenol, and alkohols have been developed by a strategy of in situ directing group formation, affording an efficient and convenient synthesis of α-alkoxyl tetrahydroquinolines from basic starting materials. A plausible mechanism involving rhodium(III) catalytic C-H functionalization and double nucleophilic attacks is proposed. The nucleophilicity order of some alcohols is also obtained for the cascade reaction.

Cascade C-H Functionalization/Amidation Reaction for Synthesis of Azepinone Derivatives.

A cascade C-H functionalization/amidation reaction of aminobiaryls with diazomalonates has been developed under rhodium catalysis, affording new azepinone derivatives in moderate to excellent yields.

Morita-Baylis-Hillman Reaction of α,β-Unsaturated Ketones with Allylic Acetates by the Combination of Transition-Metal Catalysis and Organomediation.

An intermolecular Morita-Baylis-Hillman (MBH) reaction of α,β-unsaturated ketones with allylic acetates under the catalysis of 10 mol % of tetrakis(triphenylphosphine)palladium(0) and mediation of tributylphosphine has been developed in the presence of acetic acid, affording the desired α-coupling products. The MBH reaction has the advantages of good tolerance to many functional groups, excellent regioselectivity and E-stereoselectivity, and moderate to good yields.

Dehydrogenative Cross-Coupling Reaction between N-Aryl α-Amino Acid Esters and Phenols or Phenol Derivative for Synthesis of α-Aryl α-Amino Acid Esters.

A novel dehydrogenative cross-coupling (DCC) reaction between N-arylglycine esters and phenols or 1,3,5-trimethoxybenzene was developed by copper catalysis using di-tert-butyl peroxide (DTBP) as an oxidant. Under optimized conditions, a range of N-arylglycine esters 1 underwent the DCC reaction smoothly with various phenols 2 or 1,3,5-trimethoxybenzene 4 to give desired α-aryl α -amino acid esters 3 or 5, respectively, with high ortho regioselectivities in a moderate to excellent yield. A possible mechanism involving aromatic electrophilic substitution is proposed.

Domino Reactions Containing Different Types of Heck Reactions for Selective 3,3- and 1,3-Diarylations of Propenol with Aryl Halides by Triple Catalysis.

A new domino Heck-isomerization/Saegusa/Heck reaction of propenol with aryl iodides has been developed for the synthesis of 3,3-diaryl propenals by triple transition-metal catalysis. Moreover, we also developed the domino Heck-isomerization/Heck-type reaction of propenol with aryl iodides for the synthesis of 1,3-diaryl propanones by double transition-metal catalysis and the mediation of secondary amine or triple transition metal catalysis and aminocatalysis.

A dehydrogenative cross-coupling reaction between aromatic aldehydes or ketones and dialkyl H-phosphonates for formyl or acylphenylphosphonates.

A novel DCC reaction between aromatic aldehydes or ketones and H-phosphonates has been developed for the synthesis of p-formyl or p-acylphenylphosphonates. The synthetic method has excellent para regioselectivities, good yields, and broad substrate scopes and is more benign to the environment. The DCC reaction also tolerates many functional groups, and results in a series of new p-formyl and p-acylphenylphosphonates, which should be important building blocks for the synthesis of versatile arylphosphonate derivatives.

Dehydrogenative cross-coupling reaction by cooperative transition-metal and Brønsted acid catalysis for the synthesis of β-quinolinyl α-amino acid esters.

A novel dehydrogenative cross-coupling (DCC) reaction between methylquinoline derivatives and N-aryl glycine esters was developed by a cooperative catalysis of copper salt and Brønsted acid, affording an efficient synthesis of β-quinolinyl α-amino acid esters. A plausible mechanism using a proton to activate the methylquinoline derivative and copper(II) to activate N-aryl glycine ester has been proposed.

A cascade alkylarylation reaction of 2-isocyanobiphenyls with simple alkanes for 6-alkyl phenanthridines via dual C(sp3)-H/C(sp2)-H functionalizations.

A cascade alkylarylation reaction of 2-isocyanobiphenyls with simple alkanes for 6-alkyl phenanthridines has been developed through dual C(sp(3))-H/C(sp(2))-H functionalizations. The synthetic method has the advantages of high yields, good compatibility of functional groups and mild reaction conditions, although very unreactive alkanes were involved in the reaction. A plausible mechanism through both copper-catalyzed and DTBP mediated pathways has also been proposed.

Copper-catalyzed dehydrogenative cross-coupling reaction between allylic C-H bonds and α-C-H bonds of ketones or aldehydes.

A dehydrogenative cross-coupling reaction between allylic C-H bonds and the α-C-H bond of ketones or aldehydes was developed using Cu(OTf)2 as a catalyst and DDQ as an oxidant. This synthetic approach to γ,δ-unsaturated ketones and aldehydes has the advantages of broad scope for both ketones and aldehydes as reactants, mild reaction conditions, good yields and atom economy. A plausible mechanism using Cu(OTf)2 as a Lewis acid catalyst was also proposed (DDQ=2,3-dichloro-5,6-dicyano-1,4-benzoquinone; Tf=trifluoromethanesulfonate).

Synthesis of imides by palladium-catalyzed C-H functionalization of aldehydes with secondary amides.

An efficient palladium-catalyzed C-H functionalization of aldehydes with various N-substituted N-heteroarene-2-carboxamides has been developed for the synthesis of secondary imides. The reaction tolerates various functionalities, such as methoxy, fluoro, chloro, and bromo groups. A tentative radical mechanism for a Pd(II)/Pd(IV) catalytic cycle is proposed.

Transesterification for synthesis of carboxylates using aldehydes as acyl donors via C-H and C-O bond activations.

A new type of transesterification between aryl, heteroaryl, alkyl N-heteroarene-2-carboxylates and various aldehydes by C-H and C-O bond activations has been developed for the synthesis of versatile carboxylates. A possible mechanism containing oxidative addition of acyl-O bond in parent ester and radical cleavage of sp(2) C-H bond in aldehyde is proposed.

Coupling reactions of heteroarenes with phosphites under silver catalysis.

A silver-catalyzed dehydrogenative cross-coupling reaction of substituted furans, thiophene, thioazole, and pyrrole 1a-e with dialkyl phosphites 2 was first developed to afford corresponding phosphonated products 3a-h with up to 89% yield and good regioselectivities. Moreover, an unprecedented coupling of various substituted pyridines 1f-k with dialkyl phosphites 2 using AgNO(3) as a catalyst and K(2)S(2)O(8) as an oxidant, followed by reduction with Na(2)S(2)O(3), was also realized to furnish desired pyridine phosphonates 3i-q in satisfactory yields with good regioselectivities.

Synthesis and antiproliferative activities of novel 5'-Schiff-base group substituted psoralen derivatives.

It was found that psoralen derivative could perform a Friedel-Crafts acylation smoothly with acetic anhydride to give 5'-acetylpsoralen in a 73% yield. In the presence of boron trifluoride etherate, 5'-acetylpsoralen reacted with both aromatic amines and aliphatic amine smoothly to afford 5'-Schiff-base group substituted psoralen derivatives in 72%-92% yields. The novel synthetic method has the advantages of cheap materials, mild reaction conditions, good yields and high regioselectivity in the Friedel-Crafts acylation.

3,5-Dimethyl-H-furo[3,2-g]chromen-7-one as a potential anticancer drug by inducing p53-dependent apoptosis in human hepatoma HepG2 cells.

Background/aims: Coumarins are natural compounds found in many plants that possess medical value by itself and its modified derivatives.

Method: Six novel coumarin derivatives were synthesized and examined for their potential anticancer cytotoxicity.

Result: Among the 6 derivatives, 3,5-dimethyl-(7)H-furo[3,2-g]chromen-7-one (DMFC) presented the strongest cytotoxicity against human hepatoma HepG2 cells in vitro with an IC(50) value of 8.

A cascade Heck-Aldol-Heck reaction by a combination of transition-metal catalysis and aminocatalysis.

An unprecedented cascade Heck-Aldol-Heck reaction was developed to form two C-C single bonds and one C=C double bond in one process by a combination of palladium(0) catalysis and aminocatalysis. Various aryl iodides could perform the cascade reaction with readily available propenol and formaldehyde to afford novel (E)-trisubstituted alkenes in 66-81% yields.

Copper-catalyzed cross dehydrogenative coupling reactions of tertiary amines with ketones or indoles.

A novel cross dehydrogenative coupling (CDC) reaction of N,N-dimethylanilines with methyl ketones by cooperative copper and aminocatalysis has been developed, which leads to the formation of β-arylamino ketones in 42-73% yields. Moreover, the copper-catalyzed alkylation of free (NH) indoles with N,N-dimethylanilines via CDC reaction is also presented, affording alkylated indoles in 52-78% yields.

The cascade carbo-carbonylation of unactivated alkenes catalyzed by an organocatalyst and a transition metal catalyst: a facile approach to gamma-diketones and gamma-carbonyl aldehydes from arylalkenes under air.

A novel cascade carbo-carbonylation reaction of unactivated arylalkenes with ketones or aldehydes was catalyzed by an organocatalyst and a transition metal catalyst via a SOMO-enamine under air, affording a simple approach to gamma-diketones and gamma-carbonyl aldehydes.

First example of highly stereoselective synthesis of 1,2,3-trisubstituted cyclopropanes via chiral selenonium ylides.

As the first example of the application of chiral selenonium ylides in asymmetric cyclopropanation, a new strategy for the highly stereoselective synthesis of chiral 1,2,3-trisubstituted cyclopropanes via selenonium ylides is described. The reaction afforded three stereoisomers of chiral 1,2,3-trisubstituted cyclopropanes with good yields, excellent diastereoselectivities, very high enantioselectivities (up to >99% ee), good generality and recyclability of chiral selenides. The possible pathways and models of the asymmetric cyclopropanation via the chiral selenonium ylides were also proposed to rationalize the excellent enantioselectivities and diastereoselectivities.