Synlett 2023; 34(17): 2052-2058
DOI: 10.1055/a-2107-5653
letter

DMAP-Catalyzed Domino Reactions of α-Chloroaldoxime O-Methanesulfonates and 2-Aminobenzoic Acids for the Synthesis of Quinazolinediones

Watcharadet Kaewman
,
Juthanat Kaeobamrung

This work was supported by Thailand Research Fund (Grant Number MRG6180298). Further support was generously provided by the Development and Promotion of Science and Technology Talent Project (DPST) for Mr. Kaewman. J.K. also thank the Faculty of Science, ­Research Fund.


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Abstract

Quinazolinedione derivatives were obtained from 2-aminobenzoic acids and bench-stable α-chloroaldoxime O-methanesulfonates via DMAP-catalyzed domino reactions under mild reaction conditions in one-pot fashion. Chemical transformations involved nucleophilic substitution, Tiemann rearrangement, and cyclic urea formation. The strength of nitrogen nucleophile of 2-aminobenzoic acids and the high level of carbon electrophile of α-chloroaldoxime O-methanesulfonates were crucial for the reaction outcome. An application to synthesize a quinazolinedione building block was introduced.

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Publikationsverlauf

Eingereicht: 20. Mai 2023

Angenommen nach Revision: 07. Juni 2023

Accepted Manuscript online:
07. Juni 2023

Artikel online veröffentlicht:
26. Juli 2023

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