ChemInform Abstract: SOME RECENT WORK ON SCHIFF BASES, IMINES AND IMINIUM SALTS IN SYNTHETIC HETEROCYCLIC CHEMISTRY ‐ A REVIEW

Govindachari, T. R.; Chinnasamy, P.; Rajeswari, Sundramoorthi; Чандрасекаран, С.; Premila, M. S.; Natarajan, S.; Nagarajan, K.; Pai, B. R.

doi:10.1002/chin.198433359

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“…However, only HPA ( 9 ) and 1,5-dihydrobenzo[ d ]oxepine-2,4-dione ( 174 ) were shown to react with trifluoromethyl imines ( 228 ) in an expected manner to yield, respectively, trifluoro-substituted lactams 229 and 230 . Glutaric anhydrides ( 19 ) require harsh reaction conditions and the lactams obtained ( 232 ) result from the CCR of isomeric trifluoromethyl imines ( 231 ) formed by a [ 1 , 3 ]-hydride shift under thermal conditions. In contrast, succinic and succinic-derived anhydrides did not lead to any additional products.…”

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

confidence: 99%

“…The reaction of imines with cyclic anhydrides, commonly named the Castagnoli–Cushman reaction (CCR), has been used for the last 50 years for the synthesis of a wide variety of lactams. This reaction has been partially reviewed in the past, [ 1 , 2 , 3 , 4 , 5 ] but the relevant contributions made in the field in the last few years require an up-to-date account. Here, we summarise the developments and applications of the Castagnoli–Cushman reaction from its discovery until now.…”

Section: Introductionmentioning

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%