A new synthesis of tafamidis via zinc-MsOH mediated reductive cyclisation strategy

A new synthesis of tafamidis via zinc-MsOH mediated reductive cyclisation strategy

A practical zinc-MsOH mediated intra-molecular reductive cyclisation and its application in the synthesis of tafamidis is presented starting from the readily available 3-hydroxy-4-nitrobenzoic acid as a precursor. The key reductive cyclization step involves the use of a combination of the readily av...

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Bibliographic Details
Published in:Journal of chemical sciences (Bangalore, India) Vol. 133; no. 2
Main Authors: Karumanchi, Kishore, Natarajan, Senthil Kumar, Gadde, Sunil, Vanchanagiri, Krishna, Moturu, Krishnamurthy V R
Format: Journal Article
Language:English
Published: New Delhi Springer India 01-06-2021
Springer Nature B.V
Subjects:
Aromatic compounds
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Column chromatography
Nitrobenzoic acid
Phenols
Precursors
Rapid Communication
Zinc
synthesis
Tafamidis
zinc-MsOH
reductive Cyclisation
2-aryl benzoxazoles
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Summary:A practical zinc-MsOH mediated intra-molecular reductive cyclisation and its application in the synthesis of tafamidis is presented starting from the readily available 3-hydroxy-4-nitrobenzoic acid as a precursor. The key reductive cyclization step involves the use of a combination of the readily available zinc and MsOH as the catalyst system. This methodology provides an attractive route to 2-aryl benzoxazoles from ortho -nitro phenols under mild reaction conditions. This methodology is developed on a multi-gram scale and without the need for column chromatography. Graphic abstract A new and alternative zinc-MsOH mediated intra-molecular reductive cyclisation and its application in the synthesis of tafamidis is reported starting from the readily available 3-hydroxy-4-nitrobenzoic acid as precursor. This method provides an attractive route to 2-aryl benzoxazoles from ortho -nitro phenols under mild reaction conditions.
ISSN:0974-3626
0973-7103
DOI:10.1007/s12039-021-01910-9