Visible-light photocatalyzed C-N bond activation of tertiary amines: a three-component approach to synthesize quinazolines.
Org Biomol Chem
; 22(6): 1245-1253, 2024 Feb 07.
Article
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| MEDLINE
| ID: mdl-38248577
ABSTRACT
A metal-free three-component approach has been developed to prepare 2,4-disubstituted quinazolines from o-acylanilines, trialkylamines and ammonium chloride under visible-light using eosin Y as the photocatalyst. The notable features of this work include (i) the use of tertiary amines as an alkyl synthon and triethanolamine as a C2-OH synthon; (ii) good functional group tolerance with 52%-98% yields; (iii) proof of concept with o-amino benzaldehyde as a substrate to deliver 2-methyl quinazoline 3pa; and (iv) gram-scale synthesis of compounds 3ga, 3ja and 3ma. A reductive quenching mechanism was proposed based on the control studies and redox potential values.
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MEDLINE
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En
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Org Biomol Chem
Asunto de la revista:
BIOQUIMICA
/
QUIMICA
Año:
2024
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Article