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Intramolecular azavinyl carbene-triggered rearrangement of furans.

ABSTRACT: An intramolecular rhodium-catalyzed reaction of 1-tosyl-1,2,3-triazoles with furans has been explored. The tosylimino functionality was found to play a significant chemical role participating in the subsequent domino-transformations of a key reaction intermediate. One of the reaction pathways leads to valuable 2-formyl- and 2-acetylpyridine building blocks, which could be obtained in one-pot starting from easily accessible (furan-2-ylmethyl)propargyl amines. An original method for the synthesis of highly functionalized indolizines from the obtained pyridines has been proposed.

SUBMITTER: Makarov AS

PROVIDER: S-EPMC6839507 | biostudies-literature | 2019 Oct

REPOSITORIES: biostudies-literature

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Intramolecular azavinyl carbene-triggered rearrangement of furans.

Makarov Anton S AS Uchuskin Maxim G MG Hashmi A Stephen K ASK

Chemical science 20190726 37

An intramolecular rhodium-catalyzed reaction of 1-tosyl-1,2,3-triazoles with furans has been explored. The tosylimino functionality was found to play a significant chemical role participating in the subsequent domino-transformations of a key reaction intermediate. One of the reaction pathways leads to valuable 2-formyl- and 2-acetylpyridine building blocks, which could be obtained in <i>one-pot</i> starting from easily accessible (furan-2-ylmethyl)propargyl amines. An original method for the syn ...[more]

PMID: 31803433

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