ArticleOrganic process research & development2020
Development of a Scalable and Sublimation-Free Route to MTAD.
Article in Organic process research & development, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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Who cites it
3 citing papers in PubMed.
- Molecular Complexity-Inspired Synthetic Strategies toward the Calyciphylline A-TypeJournal of the American Chemical Society · 2024Article
- Palladium-catalyzed dearomative 1,4-hydroamination.Tetrahedron · 2024Article
- Telescoped Oxidation and Cycloaddition of Urazoles to Access Diazacyclobutenes.The Journal of organic chemistry · 2022Article
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4 authors.
Funding
Abstract
The cyclic azodicarbonyl 4-methyl-1,2,4-triazoline-3,5-dione (MTAD) is a versatile and powerful reagent used mainly in cycloaddition chemistry. Though known for more than 50 years, its unsafe preparation, as well as purification by sublimation, hampered its widespread applicability on a larger scale. Herein we report a scalable and safe route to MTAD, which avoids the generation of methyl isocyanate. Moreover, we demonstrate that sublimation can be circumvented by the application of judicious oxidation conditions, followed by simple filtration. Overall, up to 25 g of MTAD was prepared in a single batch from commercial starting materials in three steps, with recrystallization serving as the only purification in the sequence. When employed in dearomative methodologies, the MTAD obtained by this protocol displayed synthetic efficiency equivalent to that of MTAD purified by sublimation.
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