Redox-Neutral and Atom-Economic Route to β-Carbolines via Gold-Catalyzed [4 + 2] Cycloaddition of Indolylynamides and Cyanamides.

Autor: Shcherbakov NV; Saint Petersburg State University, Universitetskaya Nab. 7/9, 199034 Saint Petersburg, Russian Federation., Chikunova EI; Saint Petersburg State University, Universitetskaya Nab. 7/9, 199034 Saint Petersburg, Russian Federation., Dar'in D; Saint Petersburg State University, Universitetskaya Nab. 7/9, 199034 Saint Petersburg, Russian Federation., Kukushkin VY; Saint Petersburg State University, Universitetskaya Nab. 7/9, 199034 Saint Petersburg, Russian Federation., Dubovtsev AY; Saint Petersburg State University, Universitetskaya Nab. 7/9, 199034 Saint Petersburg, Russian Federation.
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2021 Dec 17; Vol. 86 (24), pp. 17804-17815. Date of Electronic Publication: 2021 Nov 23.
DOI: 10.1021/acs.joc.1c02119
Abstrakt: Gold(I)-catalyzed [4 + 2] cycloaddition of indolylynamides and cyanamides (aminonitriles) is an efficient redox-neutral and atom-economic route to diversely substituted 1,3-diamino-β-carbolines. The protocol operates under mild conditions (Ph 3 PAuNTf 2 5 mol %, DCE, 60 °C) with a good tolerance to functional groups (23 examples and yields up to 98%). The obtained β-carboline systems represent a versatile synthetic platform with modifiable substituents for successive functionalizations. Control experiments indicate the crucial role of both the nature of reactants and the identity of employed catalysts in the developed cycloaddition.
Databáze: MEDLINE
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