The First Example of Azole-Fused Cyclic Anhydride Reacting in the Castagnoli–Cushman Way

Moreau, Ella; Dar’in, Dmitry; Krasavin, Mikhail

doi:10.1055/s-0036-1591908

Cited by 8 publications

(2 citation statements)

References 11 publications

(21 reference statements)

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“…Krasavin’s group has made a great effort in this direction. They used (for the first time) a pyrazole-fused cyclic anhydride ( 165 ) [ 93 ] to lead to the corresponding trans- CCR adducts ( 166 ) ( Scheme 53 A). Moderate 22–70% yields were obtained, possibly due to the formation of several minor by-products.…”

Section: Two-component Castagnoli–cushman Reactions (2c-ccr)mentioning

confidence: 99%

“…Imine-anhydride coupling using diacids as anhydride precursors is a valuable strategy for generating CCR adducts that cannot be obtained under conventional conditions [ 93 ]. The anhydrides are generated in situ from suitable diacids in the presence of a dehydrating agent and then undergo cycloaddition with the imines.…”

Section: Two-component Castagnoli–cushman Reactions (2c-ccr)mentioning

confidence: 99%

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The Castagnoli–Cushman Reaction

et al. 2023

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Since the first reports of the reaction of imines and cyclic anhydrides by Castagnoli and Cushman, this procedure has been applied to the synthesis of a variety of lactams, some of them with important synthetic or biological interest. The scope of the reaction has been extended to the use of various Schiff bases and anhydrides as well as to different types of precursors for these reagents. In recent years, important advances have been made in understanding the mechanism of the reaction, which has historically been quite controversial. This has helped to develop reaction conditions that lead to pure diastereomers and even homochiral products. In addition, these mechanistic studies have also led to the development of new multicomponent versions of the Castagnoli–Cushman reaction that allow products with more diverse and complex molecular structures to be easily obtained.

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Section: Two-component Castagnoli–cushman Reactions (2c-ccr)mentioning

confidence: 99%

Section: Two-component Castagnoli–cushman Reactions (2c-ccr)mentioning

confidence: 99%