Novel methylation. III. Methylation of tertiary amines such as pyridine and isoquinoline with alkyl carboxylates

Alkylation Reactions by Means of Alkanols and Carbon Monoxide: An Efficient Synthesis of Thioethers and of Caffeine from TheophyllineThe reaction of sodium or potassium thiolates with alkanols and carbon monoxide provides a versatile route to produce thioethers in excellent yields. By analogy, the potassium salt of theophylline suffers a nearly quantitative conversion to caffeine when heated with methanol under CO pressure. The mechanism of these alkylation reactions is discussed.

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An Environmentally Friendly Method for N‐Methylation of 5‐Substituted 1H‐Tetrazoles with a Green Methylating Reagent: Dimethyl Carbonate

Xie

Zhang

Liu

et al. 2014

Journal of Heterocyclic Chem

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in Wiley Online Library (wileyonlinelibrary.com).An environmentally friendly method was established for the N-methylation of the 5-substituted 1Htetrazoles with a green reagent: DMC. DABCO was the optimal catalyst, and hazardous chemicals were avoided in this protocol. A plausible catalytic mechanism is proposed, which consists of a DABCOactivated process and a thermally induced rearrangement of tetrazole carbamates.

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Novel methylation. III. Methylation of tertiary amines such as pyridine and isoquinoline with alkyl carboxylates

Cited by 3 publications

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The introduction of the amino group

The introduction of the amino group

Alkylierungsreaktionen mit Alkoholen und Kohlenmonoxid: Eine breit anwendbare Synthese von Thioethern und von Coffein aus Theophyllin

An Environmentally Friendly Method for N‐Methylation of 5‐Substituted 1H‐Tetrazoles with a Green Methylating Reagent: Dimethyl Carbonate

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