A general preparation of new types highly functional phosphorus zwitterions is realized via tandem three-component reactions using the corresponding alkanes, aldehydes, and Bu(3)P. Starting from our novel as synthetic reagents with commercially available acid chlorides in a one-step procedure provides an attractive approach toward furo[3,2-c]coumarins.

Preparation of new types highly functional benzofurans, benzothiophenes, and indoles is realized via intramolecular Wittig reactions with the corresponding ester, thioester, amide functionalities. The key intermediates, phosphorus ylides, presumably result from addition Bu3P toward aldehydes followed by acylation deprotonation. Synthesis benzofurans directly starting salicylic aldehyde derivatives acid chlorides in a one-step procedure also developed.

A new and general strategy for highly functional furo[3,4-c]coumarins related furyl coumarin derivatives has been developed, which is based on an extraordinarily facile intramolecular Wittig reaction, starting from α,β-unsaturated ketones, tributylphosphine, acyl chlorides. The phosphorus ylides were proposed to be the key intermediates constructing crucial furan ring, leading a wide variety of substituted coumarins in one step.

A general preparation of new types benzofurans, benzothiophenes and indoles is realized via chemoselective intramolecular Wittig reactions with the corresponding ester, thioester amide functionalities using in situ formed phosphorus ylides as key intermediates. The reaction conditions are very mild, numerous Michael acceptors commercially available acid chlorides can be applied efficiently a one-step procedure.

An efficient synthesis of functionalized benzofurans is achieved under mild and metal-free conditions from stable para-quinone methides by treatment with phosphine, acyl chloride, a base. This one-pot phospha-1,6-addition/O-acylation/Wittig reaction also demonstrated catalytic similar efficacy.

Abstract Stereoselective styryl derivatives have been prepared based on radical substitution (addition–elimination) of heterocycles or cyclohydrocarbons units to ( E ) ‐β ‐nitrostyrenes 1 using a common initiator benzoyl peroxide. High reactivity and selectivity with wide substrate scope were attained by this easy methodology. The reactions easily obtained one‐pot potential starting materials gave excellent trans ‐selectivity medium high yields in all cases. Synthetic utility approach has...

Reactions of (E)-beta-nitrostyrenes 1 and triethylborane 2 or tricyclohexylborane 4 in THF solution at room temperature the presence oxygen air as radical initiator generate high yields trans-alkenes (E)-3 (E)-5. Medium to different (E)-alkenes (E)-5, 7, 10, 12, 14 also can be prepared when reacts with radicals, from secondary alkyl iodides 6 8 tertiary 9, 11, 13, initiator. The generation only product explained by benzylic A and/or B intermediate mechanism is similar Scheme 1. Both (E)-...

An efficient and mild synthesis of trisubstituted furans, starting from α,β-unsaturated ketones, tributylphosphine, acyl chlorides, is described. The strategy employs the intramolecular Wittig protocol as a key step to install crucial furan ring, leading wide variety highly functional furans in one step.

An efficient organocatalytic quadruple cascade reaction resulting in spiroxindole scaffolds bearing five quaternary stereocenters is reported. The complex triggered by the scarcely explored vinylogous Michael addition of 3-alkylidene oxindoles to fully substituted enones and demonstrates usefulness latter as acceptors generating caged products 26-92% yields, 14-98% ee up >25 : 1 d.r. values.

An efficient and attractive synthesis of a series novel poly-functionalized phosphorus zwitterions was achieved via three-component reactions the corresponding functional nucleophiles, aldehydes, Bu3P in presence acidic promoter. These polysubstituted could regioselectively undergo further transformations to synthetically important furanonaphthoquinones related products intramolecular Wittig reaction. methods have potential application synthetic pharmaceutical chemistry for its facilitation...

Various geometrically pure (E)-beta-alkyl-styrenes have been synthesized by the radical NO(2) substitution of alkyl moieties generated via hydrogen abstraction followed decarbonylation from aliphatic aldehydes. These reactions, which involve a high chemical selectivity and regioselectivity constitute new route to (E)-beta-alkylstyrenes. Both aromatic aldehydes can be used in this novel reaction. When 2-allyloxybenzaldehyde was used, benzoyl added directly double bond without give...

A highly chemoselective PPh(3)-catalyzed three-component reaction of an imine, alkyl vinyl ketone, and phthalimide or succinimide is developed. Various functional adducts with high diastereoselectivities can be generated via aza-Morita-Baylis-Hillman reactions aryl-substituted imines ketones followed by Michael additions imides then epimerization.

Abstract A facile asymmetric synthetic protocol to afford 2,6‐disubstituted 4‐hydroxy‐3‐oxocyclohex‐3‐ene‐1,1‐dicarbonitriles has been developed through the domino double‐Michael addition of 1,5‐disubstituted 1‐hydroxy‐1,4‐dien‐3‐ones 2‐alkylidenemalononitriles using quinine as catalyst. This simple organocatalytic process provides access various highly functionalized chiral 4‐hydroxy‐3‐oxocyclohex‐3‐enes, which are rarely reported diketo cyclohexane analogues, in moderate‐to‐good yields and...

Reactions of salicylaldehyde (1) with β-nitrostyrenes (2), ( 4), and (6) in the presence 1,4-diazabicyclo[2.2.2]octane (DABCO) without use solvent at 40 ℃ gave high yields corresponding 3-nitrochromenes, respectively.Other conjugated nitroalkenes were also used to react under similar conditions substituted 3-nitrochromenes moderate high.96% cis-3-nitro-4-hydroxyflavane (11) was isolated as sole stereoisomer when 1 reacted 2-nitromethyleneadamantane (10) condition.When reaction temperature...

Reactions of ketones 1, nitromethane 2, and catalytic amount piperidine 3 in the presence mercaptan 6 generate beta-nitroalkyl sulfides 7-9. At 0 degrees C by use dichloromethane as solvent, 7-9 can be oxidized m-chloroperoxybenzoic acid (m-CPBA) 10 to sulfoxides 11-13 undergo elimination carbon tetrachloride solution produce medium high yield 2,2-disubstituted 1-nitroalkenes 5. The irreversibility synthetic mechanism not only overcome reversibility Henry reaction synthesis 5 but also major...

Ein süßer Zusatz: Die asymmetrische [4+2]-Cycloaddition zwischen maskierten ortho-Benzochinonen und einer Vielzahl an Alkenolen, bei der Zucker als chirale Hilfsstoffe eingesetzt werden (siehe Schema; Bn: Benzyl), liefert die optisch reinen Bicyclo[2.2.2]oct-5-en-2-one mit ausgezeichneter Diastereoselektivität in guten Ausbeuten.

The diastereoselective synthesis of 2,6-disubstituted 3-alkanoyl-4-hydroxycyclohex-3-ene-1,1-dicarbonitriles has been developed through domino double Michael addition 1,5-disubstituted 1-hydroxy-1,4-dien-3-ones to 2-alkylidenemalononitriles catalyzed by triethylamine. This simple process affords a variety highly functionalized 3-alkanoyl-4-hydroxycyclohex-3-enes, some which are not easily accessible using other methodologies, in moderate good yields and excellent diastereoselectivity (dr >...

A highly diastereoselective method for the synthesis of novel spiro-tetrahydroquinoline derivatives is reported here, using a one-pot reaction method. All compounds were characterized by 1H-nuclear magnetic resonance (NMR) and mass spectroscopy, their stereo configurations confirmed X-ray analysis. These activities these then tested in human keratocyte cells. The responses cells to treatment with selected studied scratch analysis, mouse excision wound model. Three demonstrated significant...

ABSTRACT Organocatalysts bearing sulfide or sulfone functions ( 1a , 1b 1c 1d ) were studied for the direct asymmetric Michael addition of ketones and alkylidene malonates. The organocatalyst S )‐2‐((naphthalen‐2‐ylthio)methyl)pyrrolidine, a pyrrolidine moiety, showed very high catalytic activity in absence additives. reaction condition is mild, adducts obtained good enantioselectivities (up to 96%), diastereoselectivities 95:5), chemical yields 95%). Chirality 24:600–605, 2012 . © Wiley...

Diterpenoids jolkinolide A and B, were first isolated from Euphorbia fischeriana . In our previous research, 19-(Benzyloxy)-19-oxojolkinolide B (19-BJB), a derivative of jolkinolides, was synthesized as novel ent -abietane diterpene diepoxide. this study, 19-BJB showed strong in vitro activity against bladder cancer cell lines. DNA damage which observed through the interaction with nucleotide chains affected repair resulted activation checkpoint kinase 1 (Chk1) 2 (Chk2) vivo testing nude...