One‐pot microwave‐assisted solvent free synthesis of simple alkyl 1,2,3‐triazole‐4‐carboxylates by using trimethylsilyl azide

Kheradmand, Khojasteh

doi:10.1002/jhet.36

Cited by 21 publications

(8 citation statements)

References 32 publications

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“…98 In 2009, a fast one-pot, microwave-assisted, solvent-free and high-yielding synthesis of dimethyl 1H-1,2,3-triazole-4,5-dicarboxylate (305) by 1,3-dipolar cycloaddition reaction with trimethylsilyl azide 304 and DMAD was described (Scheme 84). 99…”

Section: Azidesmentioning

confidence: 99%

Dimethyl Acetylenedicarboxylate: A Versatile Tool in Organic Synthesis

Neochoritis

Zarganes‐Tzitzikas

Stephanidou‐Stephanatou

2014

Synthesis

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This review presents the recent progress in the chemistry of dimethyl acetylenedicarboxylate (DMAD). The interest in and applications of this powerful reagent with more than 135 years of history have greatly increased in the last 10 years, further proving its versatility. Undoubtedly, DMAD can be a multi-tool in the quest of molecular complexity and diversity. The extreme structural diversity of the products described in this review illustrates the powerful potential of DMAD as a building block in organic synthesis.

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Section: Azidesmentioning

confidence: 99%

Dimethyl Acetylenedicarboxylate: A Versatile Tool in Organic Synthesis

Neochoritis

Zarganes‐Tzitzikas

Stephanidou‐Stephanatou

2014

Synthesis

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“…Taherpour et al 89 have described the solvent free one-pot MW-assisted synthesis of phthalimides and maleimides from cyclic anhydrides using KBr as solid phase and urea or thiourea as reagents.…”

Section: Methodsmentioning

confidence: 99%

Microwave-promoted synthesis of cyclic imides

Perillo¹,

Shmidt²,

Prieto³

et al. 2018

Arkivoc

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Cyclic imides have been extensively investigated because of the wide range of biological activities they exert, as well as due to their importance as synthetic intermediates. Nowadays, focus has been placed on this important class of compounds for their potential new applications, especially in the area of pharmaceutical chemistry. Consequently, the strategies applied for the synthesis of these compounds have attracted considerable attention. Several innovative methodologies have been developed to obtain and functionalize this class of compounds. The use of microwave heating, which is an environmentally harmless strategy, has been making successful inroads in many chemistry areas, such as organic synthesis. Herein we present an update of the microwave-promoted methods for the synthesis of cyclic imides.

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“…This protocol was based on a literature procedure. 50 A mixture of azidotrimethylsilane (2.6 mL, 20 mmol) and methyl propiolate 16 (1.8 mL, 20 mmol) was heated for 4 h at 90 °C, concentrated, and coevaporated with MeOH to yield the title compound as a white solid (1.74 g, 14 mmol, 68%). 1 H NMR (400 MHz, MeOD): δ 8.35 (s, 1H), 3.92 (s, 3H).…”

Section: Experimental Sectionmentioning

confidence: 99%

Structure Kinetics Relationships and Molecular Dynamics Show Crucial Role for Heterocycle Leaving Group in Irreversible Diacylglycerol Lipase Inhibitors

et al. 2019

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Drug discovery programs of covalent irreversible, mechanism-based enzyme inhibitors often focus on optimization of potency as determined by IC50-values in biochemical assays. These assays do not allow the characterization of the binding activity (Ki) and reactivity (kinact) as individual kinetic parameters of the covalent inhibitors. Here, we report the development of a kinetic substrate assay to study the influence of the acidity (pKa) of heterocyclic leaving group of triazole urea derivatives as diacylglycerol lipase (DAGL)-α inhibitors. Surprisingly, we found that the reactivity of the inhibitors did not correlate with the pKa of the leaving group, whereas the position of the nitrogen atoms in the heterocyclic core determined to a large extent the binding activity of the inhibitor. This finding was confirmed and clarified by molecular dynamics simulations on the covalently bound Michaelis–Menten complex. A deeper understanding of the binding properties of covalent serine hydrolase inhibitors is expected to aid in the discovery and development of more selective covalent inhibitors.

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One‐pot microwave‐assisted solvent free synthesis of simple alkyl 1,2,3‐triazole‐4‐carboxylates by using trimethylsilyl azide

Cited by 21 publications

References 32 publications

Dimethyl Acetylenedicarboxylate: A Versatile Tool in Organic Synthesis

Dimethyl Acetylenedicarboxylate: A Versatile Tool in Organic Synthesis

Microwave-promoted synthesis of cyclic imides

Structure Kinetics Relationships and Molecular Dynamics Show Crucial Role for Heterocycle Leaving Group in Irreversible Diacylglycerol Lipase Inhibitors

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