Smiles rearrangements in a series of berberine analogues containing a secondary acetamide fragment

Smiles rearrangements in a series of berberine analogues containing a secondary acetamide fragment Full article

Journal

Tetrahedron Letters
ISSN: 0040-4039

Output data

Year: 2014, Volume: 55, Number: 44, Pages: 6125-6127 Pages count : DOI: 10.1016/j.tetlet.2014.09.059

Tags

Smiles rearrangement; Berberine; Berberrubine; Secondary amides; Isoquinoline alkaloids

Authors

Nechepurenko Ivan V. ¹ , Komarova Nina I. ¹ , Shernyukov Andrey V. ¹ , Vasiliev Vladimir G. ¹ , Salakhutdinov Nariman F. ¹

Affiliations

1	(Данные Web of science) Russian Acad Sci, NN Vorozhtzov Novosibirsk Inst Organ Chem, Siberian Branch, Novosibirsk 630090, Russia

Smiles rearrangements occurring in the derivatives of the isoquinoline alkaloid, berberine, containing an oxyacetic acid fragment at C-9 are described. Methyl-2-(9-demethoxyberberinebromide-9-yl)oxyacetate reacts with an excess of propylamine followed by sequential aminolysis and Smiles rearrangement leading to 2-hydroxy-N-(berbero-9-yl)-N-propylacetamide in 80% yield. Reactions of berberrubine with secondary amides of bromoacetic acid via Smiles rearrangement give N-substituted 2-hydroxy-N-(berbero-9-yl)acetamides (yields 20-36%). In some cases, the intermediate secondary amides were isolated. (C) 2014 Elsevier Ltd. All rights reserved.

Nechepurenko I.V. , Komarova N.I. , Shernyukov A.V. , Vasiliev V.G. , Salakhutdinov N.F.
Smiles rearrangements in a series of berberine analogues containing a secondary acetamide fragment
Tetrahedron Letters. 2014. V.55. N44. P.6125-6127. DOI: 10.1016/j.tetlet.2014.09.059 WOS Scopus

Published print:

Oct 1, 2014

Web of science	WOS:000343625300026
Scopus	2-s2.0-84949143646
OpenAlex	W2086439094