EventsThe 3rd International Electronic Conference on Synthetic Organic Chemistry
Published
This submission belongs to the session a. General Organic Synthesis of the event The 3rd International Electronic Conference on Synthetic Organic Chemistry
Published date
01 Nov, 1999
Citation
Oleg N. Tolkachev, Alexander N. Shchavlinskii, Vladimir N. Bulavka, N-Methyltyramine and N,O-Dimethyltyramine Synthesis via Intermediate 4-Methoxyphenyl-N-methyltioacetamide., in Proceedings of The 3rd International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 1999, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-3-01731
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N-Methyltyramine and N,O-Dimethyltyramine Synthesis via Intermediate 4-Methoxyphenyl-N-methyltioacetamide.

Vladimir N. Bulavka 1
Alexander N. Shchavlinskii 2
Oleg N. Tolkachev 2
1. Scientific-Research Phototechnical Institute on Slavich Company (NIFTI-Slavich); Mendeleev sq. 2, Pereslavl-Zalesskii, Yaroslavl region, 152140, Russian Federation.
2. All-Russian Institute of Medicinal and Aromatic Plants (VILAR); Grina str., 7, Moscow, 113628, Russian Federation
Abstract
N-Methyltyramine and its alkyl or benzyl ethers are common intermediate products in the syntheses of narwedine, and galanthamine alkaloids [1-8]. They are usually produced from the corresponding arylacetamides by lithium aluminium hydride reduction. In order to avoid application of inflammable lithium aluminium hydride bulgarian scientists have transformed arylacetamide to arylthioacetamide with phosphorus (V) sulfide with following reduction of arylthioacetamide with complex sodium borohydride - nickel or cobalt chloride agents [7, 8]. Here we present a new short way route to N-methyltyramine and its ethers via the corresponding aryl-N-methylthioacetamides, shown at the scheme 1 at the example of N-methyltyramine and N,O-dimethyltyramine synthesis.
Keywords
galanthamine synthesis half-products
N-methyltyramine
N-methyltyramine ethers
N,O-dimethyltyramine
arylthioacetamide
Willgerodt-Kindler reaction
Synthesis of Heterocycles Using Tandem Cyclization Processes.
2-Methylbenzothiazole synthesis from 2-Mercaptoaniline and Acetic Acid