62358-91-2

Upstream product

• 62358-87-6 1-(3-tolyl)-3,3-diethoxyprop-1-yne 
• 625-95-6 3-Iodotoluene 
• 766-82-5 1-ethynyl-3-methyl-benzene 
• 109-94-4 formic acid ethyl ester 
• 4394-85-8 4-morpholinecarboxaldehyde 
• 16035-11-3 3-(3-methylphenyl)propargyl alcohol 
• 558-13-4 carbon tetrabromide 
• 68-12-2 N,N-dimethyl-formamide 
• 620-23-5 m-tolyl aldehyde 
• 97065-56-0 1-(2,2-dibromovinyl)-3-methylbenzene 
• 20461-86-3 2,2-diethoxy acetic acid 
• 33675-43-3 1-(bromo-ethynyl)-3-methyl-benzene 

Downstream Products

• 1203668-64-7 (E)-1-methyl-3-(4-nitrobut-3-en-1-yn-1-yl)benzene 
• 1260421-80-4 3-m-tolylprop-2-yne-1,1-diyl diacetate 
• 1322081-01-5 ethyl (R)-6-methyl-2-oxo-4-(m-tolyl)-3,4-dihydro-2H-pyran-5-carboxylate 
• 1376709-04-4 3-(diphenylmethyleneamino)-1-phenyl-4-m-tolylpyridin-2(1H)-one 
• 1604677-07-7 C₁₉H₁₅NO₃ 
• 1644539-63-8 methyl (R)-5-oxo-2-phenyl-3-(m-tolyl)-2,5-dihydrofuran-2-carboxylate 
• 1644539-82-1 methyl 5-oxo-2-phenyl-3-(m-tolyl)-2,5-dihydrofuran-2-carboxylate 

Relevant academic research and scientific papers

Synthesis of Chiral Propargylamines, Chiral 1,2-Dihydronaphtho[2,1-b]furans and Naphtho[2,1-b]furans with C-Alkynyl N,N′-di-(tert-butoxycarbonyl)-aminals and β-Naphthols

Chiral phosphoric acid-catalyzed couplings of C-alkynyl N,N′-di-(tert-butoxycarbonyl)-aminals with β-naphthols led to chiral propargylamines in moderate to high yields with high to excellent enantioselectivity, in which the reactions underwent sequential chiral phosphoric acid-catalyzed in situ formation of N-(tert-butoxycarbonyl)-imines (N-Boc-imines) from the aminals, and 1,2-addition of β-naphthols to the N-Boc-imines. Chiral 1,2-dihydronaphtho[2,1-b]furans and naphtho[2,1-b]furans were prepared with satisfactory results when 10 mol% AgOAc and 20 mol% 2,6-lutidine or 1.2 equiv. of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) were added to the resulting chiral propargylamines solution, respectively.

Transition-metal-free and facile synthesis of 3-alkynylpyrrole-2,4-dicarboxylates from methylene isocyanides and propiolaldehyde

A transition-metal-free, facile and efficient method for the synthesis of 3-alkynylpyrrole-2,4-dicarboxylates from methylene isocyanides and propiolaldehyde with moderate to good yields has been developed. The direct transformation process and good tolerance of various substituents make it an alternative approach to previous protocols, and potential applications of these investigated compounds are expected with or without post-modifications.

Catalyst-Free Annulation of 2-Pyridylacetates and Ynals with Molecular Oxygen: An Access to 3-Acylated Indolizines

A catalyst and additive-free annulation of 2-pyridylacetates and ynals under molecular oxygen was the first developed, affording 3-acylated indolizines in good to excellent yields. Molecular oxygen was used as the source of the carbonyl oxygen atom in indolizines. This approach was compatible with a wide range of functional groups, and especially it has been successfully extended to unsaturated double bonds and triple bonds, which were difficult to prepare by previous methods in a single step.

Blue light photoredox-catalysed acetalation of alkynyl bromides

Herein, we report an organo-photoredox-based protocol using 2,2-diethoxyacetic acid as the acetal source to achieve acetalation of alkynyl bromides to afford various alkynyl acetal products. In addition to arylethynyl bromides, substrates bearing heteroaryl rings (thiophene, pyridine, and indole) smoothly gave the corresponding acetalation products. This mild protocol has potential utility for the synthesis of aldehydes by further protonization.

Regioselective Synthesis of Indene from 3-Aryl Propargylic gem-Dipivalates Catalyzed by N-Heterocyclic Carbene Gold(I) Complexes

1-Aryl-3,3-bis(pivaloyloxy)propynes can be converted in good to high yields into either 1,3- or 1,2-bis(pivaloyloxy)indenes, depending on the N-heterocyclic carbene (NHC) gold(I) hexafluoroantimonate catalyst used. Almost exclusive formation of 1,3-di(oxycarbonyl)indene derivatives was achieved with cationic gold complexes containing the embracing N,N′-1,3-bis(9-butylfluorenyl)benzimidazolylidene ligand (nBuFNHC). The regioselective issue of the reaction was rationalized by the specific spatial distribution of the steric bulk in the nBuFNHC ligand. In contrast, only modest selectivities in favor of 1,2-disubstituted indenes were observed with more classical NHC gold complexes, the best selectivity being then obtained with N,N′-1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazolylidene gold chloride (SIPrAuCl) as precatalyst. (Figure presented.).

Combining silver- and organocatalysis: An enantioselective sequential catalytic approach towards pyrano-annulated pyrazoles

A one-pot asymmetric Michael addition/hydroalkoxylation sequence, catalyzed by a sequential catalytic system consisting of a squaramide and a silver salt, provides a new series of chiral pyrano-annulated pyrazole derivatives in excellent yields (up to 95%) and high enantioselectivities (up to 97% ee).

Zinc-catalyzed [4+3] cycloaddition with concomitant furan annulation: Formation of cyclohepta[b]furans

A convenient zinc-promoted [4+3] cycloaddition of a carbonyl ene-yne with simple dienes was first achieved. This reaction provided an efficient strategy to prepare various cyclohepta[b]furan rings by cascade cycloadditions. Additionally, a multicomponent reaction of dione, alkynal, and diene was also reported, which exhibited a novel strategy for selective creations of C-O bonds and C-C bonds. Go tandem! A first zinc-catalyzed tandem [4+3] cycloaddition is presented herein. Various substituted cyclohepta[b]furans were synthesized from carbonyl ene-yne and diene in moderate to good yield. Furan rings and seven-membered rings were prepared in one single step (see scheme; TBS=tert-butyldimethyl).

Combining silver catalysis and organocatalysis: A sequential michael addition/hydroalkoxylation one-pot approach to annulated coumarins

A highly stereoselective one-pot procedure for the synthesis of five-membered annulated hydroxycoumarins has been developed. By merging primary amine catalysis with silver catalysis, a series of functionalized coumarin derivatives were obtained in good yields (up to 91%) and good to excellent enantioselectivities (up to 99% ee) via a Michael addition/hydroalkoxylation reaction. Depending on the substituents on the enynone, the synthesis of annulated six-membered rings is also feasible.

Bronsted acid catalyzed and NIS-promoted cyclization of diynones: Selective synthesis of 4-pyrone, 4-pyridone, and 3-pyrrolone derivatives

Bronsted acid catalyzed tandem cyclization was found to be highly effective for the preparation of a series of polysubstituted 4-pyrones from diynones (yield up to 99%). 4-Pyridone and 3-pyrrolone derivatives were also selectively synthesized by employing NIS and/or Bronsted acid. NIS as an electrophilic reagent could promote these reactions efficiently and rapidly under very mild reaction conditions.

NOVEL SPIROHETEROCYCLIC COMPOUNDS AS MGLU5 ANTAGONISTS

The invention provides compounds having the general formula (I) wherein X is O or S; R1 is C, N, O or S; R1a is CH, CH2, N or NH; R2 is a bond, CH or CH2; m is 1, 2 or 3; n is 1 or 2; when n is 2 or m is 2 or 3, the ring containing R1 may be fused with a benzene ring; each --- represents a single or double bond provided that one double bond extends from the carbon atom to which R3-C≡C- is bonded and that no ring carbon atom bears two double bonds; and R3, R4 and R5 represent a wide range of substituents. These compounds are selective for the metabotropic mGlu5 receptor. They, their solvates, hydrates, enantiomers, diastereomers, N-oxides and pharmaceutically acceptable salts, and pharmaceutical compositions containing them, can be used to treat diseases or disorders of the lower urinary tract, especially neuromuscular dysfunctions of the lower urinary tract. They may also be useful for the treatment of migraine; for the treatment of gastroesophageal reflux disease (GERD); for the treatment of anxiety disorder; for the treatment of abuse, substance dependence and substance withdrawal disorder; for the treatment of neuropathic pain disorder; and for the treatment of fragile X syndrome disorders.