Highly specific N-monomethylation of primary aromatic amines

Pera, Adolfo Le; Leggio, Antonella; Liguori, Angelo

doi:10.1016/j.tet.2006.03.104

Cited by 31 publications

(18 citation statements)

References 52 publications

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“…Mp: 170–171°C (lit. 174–176°C) 37 ; 1 H NMR (400 MHz, CDCl 3 ) δ 8.28 (d, J = 8.8 Hz, 2H), 7.91 (d, J = 8.4 Hz, 2H), 7.29 (t, J = 6.8 Hz, 2H), 7.21 (t, J = 7.2Hz, 1H), 7.22-7.18 (m, 1H), 7.08 (d, J = 8.4 Hz, 2H), 6.57 (br s, 1H).…”

Section: Methodsmentioning

confidence: 99%

Synthesis and biological evaluation of naphthoquinone analogs as a novel class of proteasome inhibitors

Lawrence

Kazi

Luo

et al. 2010

Bioorganic & Medicinal Chemistry

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Screening of the NCI Diversity Set-1 identified PI-083 (NSC-45382) a proteasome inhibitor selective for cancer over normal cells. Focused libraries of novel compounds based on PI-083 chloronaphthoquinone and sulfonamide moieties were synthesized to gain a better understanding of the structure activity relationship responsible for chymotrypsin-like proteasome inhibitory activity. This led to the demonstration that the chloronaphthoquinone and the sulfonamide moieties are critical for inhibitory activity. The pyridyl group in PI-083 can be replaced with other heterocyclic groups without significant loss of activity. Molecular modeling studies were also performed to explore the detailed interactions of PI-083 and its derivatives with the β5 and β6 subunits of the 20S proteasome. The refined model showed an H-bond interaction between the Asp-114 and the sulfonamide moiety of the PI-083 in the β6 subunit.

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Section: Methodsmentioning

confidence: 99%

Synthesis and biological evaluation of naphthoquinone analogs as a novel class of proteasome inhibitors

Lawrence

Kazi

Luo

et al. 2010

Bioorganic & Medicinal Chemistry

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“…[3] Therefore,t o prevent overmethylation, conventional syntheses of N-monomethyl amines from primary amines require protection and deprotection steps,w hich reduce the atom efficiencyo ft he overall process. [4] Thes electivity problem has been addressed in the literature to some extent, yet most accounts have focused on the Nmonomethylation of less nucleophilic aromatic amines. [5] Limited methods have been reported for aliphatic amines (Scheme 1a).…”

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confidence: 99%

Selective Monomethylation of Amines with Methanol as the C₁ Source

Choi

Hong

2018

Angew Chem Int Ed

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The N-monomethyl functionality is a common motif in a variety of synthetic and natural compounds. However, facile access to such compounds remains a fundamental challenge in organic synthesis owing to selectivity issues caused by overmethylation. To address this issue, we have developed a method for the selective, catalytic monomethylation of various structurally and functionally diverse amines, including typically problematic primary aliphatic amines, using methanol as the methylating agent, which is a sustainable chemical feedstock. Kinetic control of the aliphatic amine monomethylation was achieved by using a readily available ruthenium catalyst at an adequate temperature under hydrogen pressure. Various substrates including bio-related molecules and pharmaceuticals were selectively monomethylated, demonstrating the general utility of the developed method.

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“…However, some of these reduction procedures may be incompatible with the presence of other labile functional groups. To control over-reaction, the use of acyl 13 or sulfonyl 14 derivatives of the starting amines as precursors is frequent, even though this requires the inclusion of protection/deprotection steps in the reaction sequence, which may be cumbersome. More recent approaches have been developed to circumvent some of these issues, such as the use of carbon dioxide 15 or MeOH 16 as C1-building blocks.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Mono-N-Methyl Aromatic Amines from Nitroso Compounds and Methylboronic Acid

Roscales

Csákÿ

2019

ACS Omega

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The selective synthesis of mono- N -methyl aromatic amines was achieved by the reaction of aromatic nitroso compounds with methylboronic acid promoted by triethylphosphite under transition metal-free conditions. The target compounds are constructed efficiently without overmethylation, under environmentally benign reaction conditions that do not require bases or reductants and therefore are of interest in pharmaceutical, agricultural, and chemical industries.

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Highly specific N-monomethylation of primary aromatic amines

Cited by 31 publications

References 52 publications

Synthesis and biological evaluation of naphthoquinone analogs as a novel class of proteasome inhibitors

Synthesis and biological evaluation of naphthoquinone analogs as a novel class of proteasome inhibitors

Selective Monomethylation of Amines with Methanol as the C₁ Source

Synthesis of Mono-N-Methyl Aromatic Amines from Nitroso Compounds and Methylboronic Acid

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Highly specific N-monomethylation of primary aromatic amines

Cited by 31 publications

References 52 publications

Synthesis and biological evaluation of naphthoquinone analogs as a novel class of proteasome inhibitors

Synthesis and biological evaluation of naphthoquinone analogs as a novel class of proteasome inhibitors

Selective Monomethylation of Amines with Methanol as the C1 Source

Synthesis of Mono-N-Methyl Aromatic Amines from Nitroso Compounds and Methylboronic Acid

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Product

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Selective Monomethylation of Amines with Methanol as the C₁ Source