Anhydride‐Based Multicomponent Reactions

Martin, Kathleen; Shaw, Jared T.; Younai, Ashkaan

doi:10.1002/9783527678174.ch13

Cited by 3 publications

(5 citation statements)

References 45 publications

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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%

Section: Introductionmentioning

confidence: 99%

The Castagnoli–Cushman Reaction

et al. 2023

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“…in the anhydride can facilitate enolate formation thus further improving its reactivity toward imines. [1,14,16,22,25] Among the anhydrides 2-5 we employed in the present study, thiodiacetic anhydride ( 5) is expected to undergo the enolization step most readily since this would produce the most stable enolized derivative. This is consistent with our experimental results and explains the inability of anhydrides 2-4 to react with imines 6 because of the less stable corresponding enolates.…”

Section: S C H E M Ementioning

confidence: 99%

Novel angularly substituted [1,4]thiazino[3,4‐a]isoquinoline carboxylic acids prepared by cyclic imine‐cyclic anhydride reaction

Pashev

Burdzhiev

Stanoeva

2022

Journal of Heterocyclic Chem

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The reaction between 1-aryl-3,4-dihydroisoquinolines and monocyclic anhydrides was studied for the first time. The method is the first one-step route to previously unknown angularly-aryl substituted racemic [1,4]thiazino[3,4-a]isoquinoline derivatives with trans configuration. It was found that electronwithdrawing substituents in the p-position of the aryl group in the starting 3,4-dihydroisoquinoline led to higher yields and shorter reaction times, which is contrary to previous observations for the reactions of homophthalic anhydride and similar acyclic N-arylmethanimines.

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“…87 Yanagimoto in 1956 discussed about the reaction between urea and PA under pressure. 88 The Martin group in 2015 published a book-chapter entitled "Anhydride-based multicomponent reactions", which contains some reactions of PA. 89 1) and 2-aminobenzimidazole (2) (Scheme 1). 90 Gitis group in 2000 reported the reaction of PA with 2methylimidazole that formed amide.…”

Section: Introductionmentioning

confidence: 99%

“… 87 Yanagimoto in 1956 discussed about the reaction between urea and PA under pressure. 88 The Martin group in 2015 published a book-chapter entitled “Anhydride-based multicomponent reactions”, which contains some reactions of PA. 89 …”

Section: Introductionmentioning

confidence: 99%