Cycloaddition of Phenyltriazolinedione with Carbazole-Alkynes and Yne-Carbamates to Access Diazacyclobutenes

Previously, we described the synthesis of stable, bicyclic examples of the rather rare diazacyclobutene (DCB) motif by means of a cycloaddition between triazolinediones and electron-rich thiolated alkynes. Here, we report the investigation of the cycloaddition of triazolinediones with related electr...

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Bibliographic Details
Published in:Journal of organic chemistry 2024-04, Vol.89 (7), p.4990-4999
Main Authors: Miller, Brock A., Narangoda, Chandima J., Kwain, Samuel, Bridges, William T., Noori, Monireh, Solomon, Erin E., Bragg, Alexis A., Sung, Alex T., Iwai, Yusuke, Ulisse, Lauren, Schmidt, William H., McMillen, Colin D., Dominy, Brian N., Whitehead, Daniel C.
Format: Article
Language:English
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Summary:Previously, we described the synthesis of stable, bicyclic examples of the rather rare diazacyclobutene (DCB) motif by means of a cycloaddition between triazolinediones and electron-rich thiolated alkynes. Here, we report the investigation of the cycloaddition of triazolinediones with related electron-rich yne-carbamates and carbazole-alkynes. Bicyclic DCBs arising from yne-carbamates were isolated in 8–65% yield, while those arising from carbazole-alkynes were isolated in 28–59% yield. Mechanistic studies and characterization of isolable byproducts shed light on the underlying issues leading to poor to moderate yields.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.4c00213