83841-91-2

Upstream product

• 16957-70-3 2-methylpent-2-enoic acid 
• 1567-14-2 methyl (2E)-2-methyl-2-pentenoate 
• 133181-02-9 3-hydroxy-2-methylene-pentanoic acid methyl ester 
• 1617-40-9 ethyl (E)-2-methyl-2-pentenoate 
• 623-36-9 (E)-2-methylpent-2-enal 
• 146984-85-2 ethyl (E)-2-iodo-2-pentenoate 
• 55314-57-3 ethyl pent-2-ynoate 
• 1838-77-3 4-methyl-5-hexen-3-ol 
• 159999-59-4 2-(acetoxyethylmethyl)acrylic acid methyl ester 

Downstream Products

• 90936-96-2 2,3-dihydro-2-ethyl-3-methyl-5-ethoxycarbonyl-6-phenyl-4-pyrone 
• 96623-45-9 2-methyl-4'-isopropyl-2-pentenoyl anilide 
• 1316008-82-8 (Z)-N-trityl-2-methyl-3-pentenamide 
• 1316008-83-9 (E)-N-trityl-2-methyl-2-pentenamide 
• 760197-72-6 2-methyl-pent-2-enoic acid 1-[hydroxy(diphenyl)methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 
• 613672-55-2 trans-2-benzyl-3-ethyl-4-methylisoxazolidin-5-one 
• 613672-55-2 trans-2-benzyl-3-ethyl-4-methylisoxazolidin-5-one 

Relevant academic research and scientific papers

Palladium-Catalyzed Regioselective C-H Functionalization/Annulation Reaction of Amides and Allylbenzenes for the Synthesis of Isoquinolinones and Pyridinones

A regioselective C-H functionalization/annulation reaction of N-sulfonyl amides and allylbenzenes through a palladium-catalyzed C(sp2)-H allylation/aminopalladation/β-H elimination/isomerization sequence has been reported. Various aryl and alkenyl carboxamides are found to be efficient substrates to construct isoquinolinones and pyridinones in up to 96% yield. Using ambient air as the terminal oxidant is another advantage regarding environmental friendliness and operational simplicity.

Stereospecific Electrophilic Fluorocyclization of α,β-Unsaturated Amides with Selectfluor

An efficient fluorocyclization of α,β-unsaturated amides through a formal halocyclization process is developed. The reaction proceeds under transition-metal-free conditions and leads to the formation of fluorinated oxazolidine-2,4-diones with excellent regio- and diastereoselectivity. The evaluation of the reaction mechanism based on preliminary experiments and density functional theory calculations suggests that a synergetic syn-oxo-fluorination occurs and is followed by an anti-oxo substitution reaction. The reaction opens a new window in the field of stereospecific fluorofunctionalization.

Nucleophilic halo-michael addition under lewis-base activation

A simple and general conjugate nucleophilic halogenation is presented. The THTO/halosilane combination has shown the ability to act as a nucleophilic halide source in the conjugate addition to a variety of Michael acceptors. In addition, a straightforward diastereoselective halogen installation using α,β-unsaturated acyloxazolidinones as platforms has been developed.

Iron-Catalyzed C?H Alkynylation through Triazole Assistance: Expedient Access to Bioactive Heterocycles

Triazole assistance enabled the first iron-catalyzed C?H alkynylation of arenes, heteroarenes, and alkenes. The modular TAM directing group set the stage for a sequential C?H alkynylation/annulation strategy with ample scope, enabling the iron-catalyzed assembly of isoquinolones, pyridones, pyrrolones, and isoindolinones with high levels of chemo-, site-, and regioselectivity.

Catalytic Enantioselective Nazarov Cyclization

A detailed account of an asymmetric Nazarov cyclization that leads to α-hydroxycyclopentenones bearing either vicinal, all-carbon quaternary centers, or vicinal quaternary and tertiary centers is given. The all-aliphatic examples represent the greatest challenge, as the dienone starting materials are not activated toward cyclization by an aryl group. The rational design and optimization of the substrates in parallel with optimization of the chiral Br?nsted acid catalyst is also described, as well as a series of diastereoselective transformations of a fully substituted cyclopentenone product.

Enantioselective palladium(0)-catalyzed nazarov-type cyclization

A Pd0-catalyzed asymmetric Nazarov-type cyclization is described. The optimized ligand for the reaction incorporates a weakly coordinating pyridine ring into a TADDOL-derived phosphoramidite (TADDOL=α,α,α,α-tetraaryl-1,3-dioxolane-4,5-dimethanol). The reaction leads to the formation of cyclopentenones as single diastereoisomers that incorporate two contiguous asymmetric centers, one tertiary and one an all-carbon-atom quaternary stereocenter, in high yield and optical purity. It is noteworthy that the reaction does not require that substrates should be activated by aryl substituents.

PROCESS FOR SYNTHESIS OF INDENES

The present invention relates to a new process for the synthesis of 2,3,4,5,6,7-substiuted indenes, which are useful precursors for the formation of certain ansa-metailocene catalysts.

Ligand-promoted alkylation of C(sp3)-H and C(sp2)-H bonds

9-Methylacridine was identified as a generally effective ligand to promote a Pd(II)-catalyzed C(sp3) - H and C(sp2) - H alkylation of simple amides with various alkyl iodides. This alkylation reaction was applied to the preparation of unnatural amino acids and geometrically controlled tri- and tetrasubstituted acrylic acids.

Nickel-catalyzed direct alkylation of C-H bonds in benzamides and acrylamides with functionalized alkyl halides via bidentate-chelation assistance

The alkylation of the ortho C-H bonds in benzamides and acrylamides containing an 8-aminoquinoline moiety as a bidentate directing group with unactivated alkyl halides using nickel complexes as catalysts is described. The reaction shows high functional group compatibility. In reactions of meta-substituted aromatic amides, the reaction proceeds in a highly selective manner at the less hindered C-H bond.

Novel (S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acids: Peroxisome proliferator-activated receptor γ selective agonists with protein-tyrosine phosphatase 1B inhibition

A novel series of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid derivatives were synthesized and (S)-2-[(2E,4E)-hexadienoyl]-7-(2-{5-methyl-2- [(1E)-5-methylhexen-1-yl]oxazol-4-yl}ethoxy)-1,2,3,4-tetrahydroisoquinoline-3- carboxylic acid (14i) was identified as a potent human peroxisome proliferator-activated receptor γ (PPARγ) selective agonist (EC 50 = 0.03 μM) and human protein-tyrosine phosphatase 1B (PTP-1B) inhibitor (IC50 = 1.18 μM). Cmax after oral administration of 14i at 10 mg/kg was 2.2 μg/ml (4.5 μM) in male SD rats. Repeated administration of 14i and rosiglitazone for 14 days dose-dependently decreased plasma glucose levels, ED50 = 4.3 and 23 mg/kg/day, respectively, in male KK-Ay mice. In female SD rats, repeated administration of 14i at 12.5-100 mg/kg/day for 28 days had no effect on the hematocrit value (Ht) and red blood cell count (RBC), while rosiglitazone significantly decreased them from 25 mg/kg/day. In conclusion, 14i showed about a fivefold stronger hypoglycemic effect and fourfold or more weaker hemodilution effect than rosiglitazone, indicating that 14i is 20-fold or more safer than rosiglitazone. Compound 14i is a promising candidate for an efficacious and safe anti-diabetic drug targeting PPARγ and PTP-1B.