Consecutive Four-Component Coupling-Addition Aza-Anellation Pictet–Spengler Synthesis of Tetrahydro-β-Carbolines: An Optimized Michael Addition and Computational Study on the Aza-Anellation Step

Autor:	Kai Ries, Françoise A. Aouane, Thomas J. J. Müller
Jazyk:	angličtina
Rok vydání:	2023
Předmět:	aza-Michael addition tetrahydro-β-carbolines catalysis one-pot reaction multicomponent reaction ytterbium (III) triflate Organic chemistry QD241-441
Zdroj:	Organics, Vol 4, Iss 3, Pp 313-332 (2023)
Druh dokumentu:	article
ISSN:	2673-401X
DOI:	10.3390/org4030025
Popis:	Starting from acid chlorides, alkynes, tryptamines, and acryloyl chloride, 21 densely substituted tetrahydro-β-carbolines were prepared in a four-component, one-pot reaction. In this study, the aza-Michael addition step to generate intermediate enaminones was optimized in the presence of ytterbium triflate. Moreover, apart from acryloyl chloride, all reactants could be deployed in almost equimolar ratios, which increases the atom economy of the sequence. For mechanistic rationalization, the concluding aza-anellation was investigated by DFT calculations on potential intermediates and corresponding activation energies, revealing that the aza-anellation proceeds via ene reaction rather than via electrocyclization.
Databáze:	Directory of Open Access Journals
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