Simplified Version of the Eschweiler-Clarke Reaction.


Journal

The Journal of organic chemistry
ISSN: 1520-6904
Titre abrégé: J Org Chem
Pays: United States
ID NLM: 2985193R

Informations de publication

Date de publication:
16 Feb 2024
Historique:
medline: 16 2 2024
pubmed: 16 2 2024
entrez: 16 2 2024
Statut: aheadofprint

Résumé

The traditional Eschweiler-Clarke reaction is a three-component process involving formaldehyde, amine, and formic acid. In this work, we showed that the reductive potential of formaldehyde was sufficient to provide methylation of secondary amines in the absence of acidic additives. Various acid-sensitive moieties remain intact under developed conditions. The scalability of the elaborated approach was shown for several products. Synthesis of the antifungal agent butenafine demonstrated the preparative utility of the developed approach.

Identifiants

pubmed: 38362854
doi: 10.1021/acs.joc.3c02476
doi:

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Auteurs

Klim O Biriukov (KO)

A. N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Vavilova St. 28, bld. 1, INEOS, 119334 Moscow, Russia.

Evgeniya Podyacheva (E)

A. N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Vavilova St. 28, bld. 1, INEOS, 119334 Moscow, Russia.
National Research University Higher School of Economics, Miasnitskaya Str. 20, 101000 Moscow, Russian Federation.

Ignatii Tarabrin (I)

Moscow South-Eastern School named after V. I. Chuikov (Moscow Chemical Lyceum), Tamozhenniy proezd 4, 111033 Moscow, Russian Federation.

Oleg I Afanasyev (OI)

A. N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Vavilova St. 28, bld. 1, INEOS, 119334 Moscow, Russia.
Plekhanov Russian University of Economics, Stremyanny per. 36, 117997 Moscow, Russian Federation.

Denis Chusov (D)

A. N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Vavilova St. 28, bld. 1, INEOS, 119334 Moscow, Russia.
National Research University Higher School of Economics, Miasnitskaya Str. 20, 101000 Moscow, Russian Federation.

Classifications MeSH