Asymmetric Synthesis of Vabicaserin via Oxidative Multicomponent Annulation and Asymmetric Hydrogenation of a 3,4-Substituted Quinolinium Salt

Dragan, V. A.; McWilliams, J. Christopher; Miller, Ross A.; Sutherland, Karen; Dillon, John L.; O’Brien, Michael K.

doi:10.1021/ol401029k

Cited by 19 publications

(8 citation statements)

References 35 publications

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“…These reactions allow the generation of complex compounds from simple raw materials in one-step. Scheme 7 always portrays a multicomponent coupling process for the synthesis of vabicaserin [17][18][19][20]. The synthesis of azoindole is also a multicomponent reaction that involves simple ketones and the haloaminpyridines.…”

Section: Via Multicomponent Couplingmentioning

confidence: 99%

Untitled

Sapra¹,

Patel²,

Meshram³

2020

J. Med. Chem. Sci.

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Novel developments in the synthetic techniques that facilitate rapid access to various functionalized heterocyclic compounds are essential in medicinal chemistry. They enable an expansion of the available drug-associated chemical space and enhance the efficiency of drug delivery. In addition, the creation of more robust synthetic techniques that can increase the drug yield can enhance the drug production rate. While researchers and manufacturers utilize established synthetic techniques during a program aimed at drug discovery, the innovation of heterocyclic synthesis processes that permit varied bond formation strategies is influencing the pharmaceutical industry in the most significant way. This review focuses on the utilization of some novel methods of activation of the C-H bonds, hydrogen borrowing catalysis, photoredox chemistry, regio-and stereoselective synthesis, and multi component reactions for the functionalization and creation of heterocycles that aided in driving project delivery.

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Section: Via Multicomponent Couplingmentioning

confidence: 99%

Untitled

Sapra¹,

Patel²,

Meshram³

2020

J. Med. Chem. Sci.

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“…The authors also found (by measure of infrared CO stretching frequencies) dimethyl-substituted phospholes are more electron-donating than either alkyl-or aryl-substituted phosphines; in their screening efforts, increased ligand electrondonating ability had appeared to correlate with improved enantioselectivity. In 2013, Dragan, McWilliams, and Miller [41] used [Ir(cod)Cl] 2 and the chiral phosphoramidite (S)-MorPhos to enantioselectively hydrogenate the quinolinium core of a precursor to the potential anti-psychotic agent Vabicaserin (Scheme 11). Addition of P( t Bu) 3 and LiCl were found to improve catalyst activity and enantioselectivity respectively.…”

Section: Asymmetric Hydrogenationmentioning

confidence: 99%

Homogeneous metal catalysis for conversion between aromatic and saturated compounds

Giustra

Ishibashi

Liu

2016

Coordination Chemistry Reviews

107

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In the past few decades, homogeneous catalysis of arene and heteroarene reduction has grown into a mature research field. In particular, hydrogenation of heteroaromatic systems facilitates rapid access to many classes of fine chemicals and pharmaceutically relevant compounds. In this review, we discuss the advancements made in the field of homogeneous metal-catalyzed arene and heteroarene hydrogenation from its early beginnings to the present day. We also review homogeneous catalysts for the reverse dehydrogenation of cyclic saturated species back to their aromatic counterparts, as well as single-catalyst systems capable of performing reversible hydrogenationdehydrogenation reactions.

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“…Compounds containing the tetrahydrobenzodiazepine moiety find numerous applications in medicinal chemistry, for example, BMS-214662, which exhibits potent antitumor activity (Figure ). , Also tetrahydrobenzodiazepines have been used as intermediates in organic synthesis. − Compounds that possess the imidazopyridine moiety display antitumor, antifungal, antibacterial, antiviral, and antiprotozoal activities, − and some are currently marketed drugs such as zolpidem used for the treatment of sleep disorder (Figure ), anxyolitic drug alpidem and antiulcer drug zolimidine . Tetrahydroquinoxalines have been studied as potent cholesteryl ester transfer protein inhibitors (Figure ), anticonvulsants, potassium channel openers, and anti-HIV agents …”

Section: Introductionmentioning

confidence: 99%

Regioselective Opening of Nitroepoxides with Unsymmetrical Diamines

2018

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Nitroepoxides are easily transformed into benzodiazepines, tetrahydrobenzodiazepines, imidazopyridines, and N-alkyl tetrahydroquinoxalines by treatment with 2-aminobenzylamines, 2-aminopyridines, and N-alkyl 1,2-diaminobenzenes, respectively. Regioselectivity is controlled through attack of the most nucleophilic nitrogen of the unsymmetrical diamine to the β position of the epoxide. These reactions represent an efficient way to prepare privileged bioactive structures.

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Asymmetric Synthesis of Vabicaserin via Oxidative Multicomponent Annulation and Asymmetric Hydrogenation of a 3,4-Substituted Quinolinium Salt

Cited by 19 publications

References 35 publications

Untitled

Untitled

Homogeneous metal catalysis for conversion between aromatic and saturated compounds

Regioselective Opening of Nitroepoxides with Unsymmetrical Diamines

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