13901-86-5

Upstream product

• 123-76-2 levulinic acid 
• 2919-20-2 1,1-di(p-tolyl)ethylene 
• 14284-89-0 manganese(III) acetylacetonate 
• 142605-86-5 6,6-bis(4-methylphenyl)-3-methyl-1,2-dioxan-3-ol 
• 104-87-0 4-methyl-benzaldehyde 
• 78-94-4 methyl vinyl ketone 
• 201230-82-2 carbon monoxide 
• 5720-05-8 4-methylphenylboronic acid 
• 66117-64-4 di(p-tolyl)borinic acid 
• 116-11-0 2-Methoxypropene 
• 619-41-0 4-(bromoacetyl)toluene 
• 2227-58-9 3-(4-methylphenyl)prop-2-ynoic acid 
• 67-64-1 acetone 
• 74032-45-4 S-2-pyridyl 4-methylbenzothiolate 

Downstream Products

• 65564-87-6 3-(4-Methylphenyl)-2-cyclopenten-1-one 
• 1609193-04-5 (2S,5S)-2-methyl-5-(p-tolyl)pyrrolidine 
• 1609192-89-3 (2S,5R)-2-methyl-5-(p-tolyl)pyrrolidine 
• 1309456-79-8 (+)-(R)-5-methyl-2-(4'-methylphenyl)-1-pyrroline 
• 1458715-56-4 5,6,7-trimethoxy-2-(4-(2-methyl-5-p-tolyl-1H-pyrrol-1-yl)phenyl)benzo[d]thiazole 
• 1458715-50-8 6-methoxy-2-(4-(2-methyl-5-p-tolyl-1H-pyrrol-1-yl)phenyl)benzo[d]thiazole 
• 1458715-45-1 6-fluoro-2-(4-(2-methyl-5-p-tolyl-1H-pyrrol-1-yl)phenyl)benzo[d]thiazole 
• 1458715-40-6 2-(4-(2-methyl-5-p-tolyl-1H-pyrrol-1-yl)phenyl)benzo[d]thiazole 
• 1445874-23-6 1-(3,4-dichlorophenyl)-2-methyl-5-p-tolyl-1H-pyrrole 
• 1445874-51-0 (R)-3-(4-(4-((1-(3,4-dichlorophenyl)-2-methyl-5-p-tolyl-1H-pyrrol-3-yl)methyl)piperazin-1-yl)-3-fluorophenyl)-5-((4-phenyl-1H-1,2,3-triazol-1-yl)methyl)oxazolidin-2-one 
• 1445874-30-5 (R)-5-(azidomethyl)-3-(4-(4-((1-(3,4-dichlorophenyl)-2-methyl-5-p-tolyl-1H-pyrrol-3-yl)methyl)piperazin-1-yl)-3-fluorophenyl)oxazolidin-2-one 
• 1258428-47-5 2-methyl-5-[4-(methyl)phenyl]-1-[4-(methoxy)phenyl]-1H-pyrrole 
• 929989-09-3 2-methyl-1-(4-chlorophenyl)-5-(4-methylphenyl)-1H-pyrrole 
• 908292-42-2 1-(4-fluorophenyl)-2-methyl-5-(4-methylphenyl)-1H-pyrrole 

Relevant academic research and scientific papers

Visible-Light Photocatalytic Preparation of 1,4-Ketoaldehydes and 1,4-Diketones from α-Bromoketones and Alkyl Enol Ethers

A Ru2+-photocatalyzed, visible-light-mediated ATRA reaction for the straightforward preparation of 1,4-ketoaldehydes, 1,4-diketones, and 1,4-ketoesters, which are of difficult access by other means, is reported herein. This method employs readily accessible α-bromoketones and alkyl vinyl ethers as starting materials, allowing the construction of secondary, tertiary, and challenging quaternary centers. In addition, the synthetic usefulness of this method is illustrated by applying it to the construction of substituted pyrroles.

Copper-Catalyzed Decarboxylative Oxyalkylation of Alkynyl Carboxylic Acids: Synthesis of ?-Diketones and ?-Ketonitriles

A novel copper-catalyzed decarboxylative oxyalkylation of alkynyl carboxylic acids with ketones and alkylnitriles via direct C(sp3)-H bond functionalization to construct new C-C bonds and C-O double bonds was developed. This transformation is featured by wide functional group compatibility and the use of readily available reagents, thus affording a general approach to ?-diketones and ?-ketonitriles. A possible mechanism is proposed.

Nonclassical Mechanism in the Cyclodehydration of Diols Catalyzed by a Bifunctional Iridium Complex

1,4- and 1,5-diols undergo cyclodehydration upon treatment with cationic N-heterocyclic carbene (NHC)–IrIII complexes to give tetrahydrofurans and tetrahydropyrans, respectively. The mechanism was investigated, and a metal-hydride-driven pathway was proposed for all substrates, except for very electron-rich ones. This contrasts with the well-established classical pathways that involve nucleophilic substitution.

One-pot synthesis of 2-methyl-1,5-diaromatic-1H-pyrroles from styrene, acetone and arylamines using TBHP, copper(II) trifluoromethanesulfonate and sulfamic acid

The one-pot copper/manganese co-catalyzed heterocyclization of arylamine derivatives with styrene and acetone to produce a series of 2-methyl-1,5-diaromatic-1H-pyrroles was investigated. The described reaction combines 1,4-dicarbonyl synthesis and Paal-Knorr type condensation reactions.

Light-Driven Vitamin B12-Catalysed Generation of Acyl Radicals from 2-S-Pyridyl Thioesters

Acyl radicals are invaluable intermediates in organic synthesis, however their generation remains challenging. Herein, we present an unprecedented light-driven, cobalt-catalysed method for the generation of acyl radicals from readily available 2-S-pyridyl thioesters. The synthetic potential of this methodology was demonstrated in the Giese-type acylation of activated olefins in the presence of heptamethyl cobyrrinate. This vitamin B12 derivative proved to be the most efficient catalyst in the studied process. The developed method features broad substrate scope (38 examples), good functional group tolerance, and mild reaction conditions. Moreover, it is easily scalable (illustrated on a 20-fold scale-up procedure), enabling its preparative use. Mechanistic studies revealed that the reaction proceeds via a radical pathway with the key steps involving the formation of an acyl-vitamin B12 complex and subsequent photolysis of the Co?C bond. (Figure presented.).

Palladium-Catalyzed Room-Temperature Acylative Suzuki Coupling of High-Order Aryl Borons with Carboxylic Acids

This note describes a dimethyl dicarbonate-assisted, Pd(OAc)2/PPh3-catalyzed acylative Suzuki coupling of carboxylic acids with diarylborinic acids or tetraarylboronates for practical and efficient synthesis of sterically undemanding aryl ketones at room temperature. More than just cost-effective alternatives to aryl boronic acids, diarylborinic acids and tetraarylboronates displayed higher reactivity in the acylative Suzuki coupling. A variety of alkyl aryl ketones, including those bearing a hydroxy, bromo, or carbonyl group, could be readily obtained in modest to excellent yields.

Copper/Manganese Cocatalyzed Oxidative Coupling of Vinylarenes with Ketones

A novel copper/manganese cocatalyzed direct oxidative coupling of terminal vinylarenes with ketones via C(sp3)-H bond functionalization following C-C bond formation has been developed using tert-butyl hydroperoxide as the radical initiator. Various ketones underwent a free-radical addition of terminal vinylarenes to give the corresponding 1,4-dicarbonyl products with excellent regioselectivity and efficiency through one step. A possible reaction mechanism has been proposed.

A regio- and stereoselective ω-transaminase/monoamine oxidase cascade for the synthesis of chiral 2,5-disubstituted pyrrolidines

Biocatalytic approaches to the synthesis of optically pure chiral amines, starting from simple achiral building blocks, are highly desirable because such motifs are present in a wide variety of important natural products and pharmaceutical compounds. Herein, a novel one-pot ω-transaminase (TA)/monoamine oxidase (MAO-N) cascade process for the synthesis of chiral 2,5-disubstituted pyrrolidines is reported. The reactions proceeded with excellent enantio- and diastereoselectivity (>94 % ee; >98 % de) and can be performed on a preparative scale. This methodology exploits the complementary regio- and stereoselectivity displayed by both enzymes, which ensures that the stereogenic center established by the transaminase is not affected by the monoamine oxidase, and highlights the potential of this multienzyme cascade for the efficient synthesis of chiral building blocks. Mirror mirror on the wall: A ω-transaminase (ω-TA)/monoamine oxidase (MAO-N) cascade process for the asymmetric synthesis of chiral 2,5-disubstituted pyrrolidines is reported. The methodology exploits the complementary regio- and stereoselectivity displayed by both enzymes, which ensures that the stereogenic center established by the TA reaction is not affected by the MAO-N catalyzed step. Copyright

Anti-tubercular agents. Part 7: A new class of diarylpyrrole-oxazolidinone conjugates as antimycobacterial agents

In an effort to discover new anti-tubercular agents, a series of new diarylpyrrole-oxazolidinone conjugates have been designed and synthesized. The anti-tubercular activity of these new conjugates (4a-n and 5a-d) against Mycobacterium tuberculosis H3

Synthesis and study of benzothiazole conjugates in the control of cell proliferation by modulating Ras/MEK/ERK-dependent pathway in MCF-7 cells

By applying a methodology, a series of benzothiazole-pyrrole based conjugates (4a-r) were synthesized and evaluated for their antiproliferative activity. Compounds such as 4a, 4c, 4e, 4g-j, 4m, 4n, 4o and 4r exhibited significant cytotoxic effect in the MCF-7 cell line. Cell cycle effects were examined for these conjugates at 2 μM as well as 4 μM concentrations and FACS analysis show an increase of G2/M phase cells with concomitant decrease of G1 phase cells thereby indicating G2/M cell cycle arrest by them. Interestingly 4o and 4r are effective in causing apoptosis in MCF-7 cells. Moreover, 4o showed down regulation of oncogenic expression of Ras and its downstream effector molecules such as MEK1, ERK1/2, p38 MAPK and VEGF. The apoptotic aspect of this conjugate is further evidenced by increased expression of caspase-9 in MCF-7 cells. Hence these small molecules have the potential to control both the cell proliferation as well as the invasion process in the highly malignant breast cancers.