Chemo‐Enzymatic One‐Pot Two‐Step Functionalization of 1,2,3,4‐Tetrahydroisoquinolines by Monoamine Oxidase‐Ugi‐Joullié Reaction Sequence.

Autor:	Barna, Bence, Gáti, Tamás, Kotschy, András, Tasnádi, Gábor
Předmět:	MONOAMINE oxidase TETRAHYDROISOQUINOLINES ORGANIC synthesis PHARMACEUTICAL chemistry CARBOXYLIC acids ISOCYANIDES MONOAMINE transporters
Zdroj:	European Journal of Organic Chemistry; 2/24/2022, Vol. 2022 Issue 8, p1-9, 9p
Abstrakt:	A one‐pot two‐step chemo‐enzymatic approach for the functionalization of substituted 1,2,3,4‐tetrahydroisoquinolines (THIQs) was developed. The system combines monoamine oxidase (MAO)‐catalyzed imine formation with Ugi‐type three‐component reaction in an aqueous buffer without intermediate isolation. The two steps were separately optimized for buffer and pH to obtain the expected products. MAOs enabled the functionalization of fifteen THIQs by oxidation to imines, while the Ugi‐Joullié‐reaction was successfully carried out with eight carboxylic acids and eight isonitriles. 41 products were isolated giving access to valuable building blocks for medicinal chemistry applications. Gram‐scale transformation demonstrated the utility of the described protocol for organic synthesis. [ABSTRACT FROM AUTHOR]
Databáze:	Complementary Index
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