Iminium Ion and <i>N</i>-Hydroxyimide as the Surrogate Components in DEAD-Promoted Oxidative Ugi Variant

Wang, Jiankun; Sun, Yilin; Jiang, Muhan; Hu, Tian-Yu; Zhao, Yan; Li, Xin; Wang, Guangji; Hao, Kun; Zhen, Le

doi:10.1021/acs.joc.8b01868

Cited by 19 publications

(11 citation statements)

References 52 publications

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“…Zhen et al developed an innovative strategy for the synthesis of N -alkyl- N -acylaminophthalimide 162a and N -alkyl- N -acylaminosuccinimide 162b through metal-free oxidative JUS-3CR by employing tertiary amine 159 as an imine surrogate, N -hydroxyimide 160 as an acid surrogate, isocyanides 5 , and DEAD 161 as an oxidant (Scheme ). This approach contains a broad substrate scope and desired functional group tolerance, which leads to an extensive range of N -alkyl- N -acylaminophthalimide 162a and N -alkyl- N -acylaminosuccinimide 162b derivatives in good yields.…”

Section: Cyclic Imines In Joulliè−ugi Reactionmentioning

confidence: 99%

Cyclic Imines in Ugi and Ugi-Type Reactions

et al. 2020

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Ugi four-component reactions (U-4CRs) are widely recognized as being highly efficient for the synthesis of pseudopeptides. However, the products of these reactions are not so interesting as drug candidates because they are not conformationally restricted enough for a potent interaction with biological targets. One possible way to overcome this problem is to replace amine and oxo components in the U-4CRs with cyclic imines in so-called Joullié−Ugi three-component reactions (JU-3CRs). This approach provides a robust single-step route to peptide moieties connected to N-heterocyclic motifs that are found as core skeletons in many natural products and pharmaceutical compounds. JU-3CRs also provide much better diastereoselectivity than their four-component analogues. We survey here the redesign of many synthetic routes for the efficient preparation of a wide variety of three-, five-, six-, and seven-membered heterocyclic compounds connected to the peptide backbone. Additionally, in the Ugi reactions based on the cyclic imines, α-acidic isocyanides, or azides can be replaced with normal isocyanides or acids, respectively, leading to the synthesis of N-heterocycles attached to oxazoles or tetrazoles, which are of great pharmaceutical significance. This Review includes all research articles related to Ugi reactions based on the cyclic imines to the year 2020 and will be useful to chemists in designing novel synthetic routes for the synthesis of individual and combinatorial libraries of natural products and drug-like compounds.

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Section: Cyclic Imines In Joulliè−ugi Reactionmentioning

confidence: 99%

Cyclic Imines in Ugi and Ugi-Type Reactions

et al. 2020

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“…Quite recently, our group explored two types of DEADpromoted oxidative Ugi-type reactions of tertiary amines. 16,17 We have been committed to broadening the application range of DEAD-assisted oxidations, which prompted us to explore the [3 + 2] cycloaddition-based synthesis of pyrrolo [2,1a]isoquinoline.…”

Section: ■ Introductionmentioning

confidence: 99%

Diethyl Azodicarboxylate-Promoted Oxidative [3 + 2] Cycloaddition for the Synthesis of Pyrrolo[2,1-a]isoquinolines

Wang

et al. 2020

J. Org. Chem.

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A novel metal-free protocol for the effective and efficient construction of pyrrolo[2,1-a]isoquinolines via a diethyl azodicarboxylate (DEAD)-promoted oxidative [3 + 2] cycloaddition/aromatization tandem reaction is described. Instead of the reported two-component oxidation systems, DEAD, as the sole oxidant, could smoothly transfer the tertiary amines to azomethine ylides via oxidation-deprotonation tandem process. The reaction proceeded with a broad substrate scope, giving rise to products in moderate to good isolated yields.

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“…Same research group further developed a novel DEAD promoted oxidative Ugi-type reaction where imine surrogates and acid surrogates were employed for the transformation. [35] N-Phenyl tetrahydroisoquinolines were used as imine surrogates and N-hydroxyphthalimide (NHPI) or N-hydroxysuccinimide (NHS) were utilized as acid surrogates (Scheme 14). The optimization studies revealed that the dual-surrogate Ugi-type reaction occurred smoothly in chlorinated solvents at room temperature.…”

Section: Oxidative Ugi-type Reactionsmentioning

confidence: 99%

Progress of Dialkyl Azodicarboxylates in Organic Transformations

Singh

Mritunjay

2021

Asian J Org Chem

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In recent past, dialkyl azodicarboxylates have been embraced as versatile reagents in synthetic strategies other than Mitsunobu reactions. These azo compounds have been utilized as an oxidant or dehydrogenating reagent in oxidative transformations, such as cross dehydrogenative coupling, oxidative Ugi-type reaction, dehydrogenation etc. Moreover, they have been utilized in different types of bond construction like C-Heteroatom (C-Het) and SÀ N bond. Very recently, these azo compounds have also been explored in photochemical reactions. Such types of reported reactions and their reaction pathways are presented here in this minireview, which manifested the oxidative abilities and advantageous features of dialkyl azodicarboxylates.

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Iminium Ion and N-Hydroxyimide as the Surrogate Components in DEAD-Promoted Oxidative Ugi Variant

Cited by 19 publications

References 52 publications

Cyclic Imines in Ugi and Ugi-Type Reactions

Cyclic Imines in Ugi and Ugi-Type Reactions

Diethyl Azodicarboxylate-Promoted Oxidative [3 + 2] Cycloaddition for the Synthesis of Pyrrolo[2,1-a]isoquinolines

Progress of Dialkyl Azodicarboxylates in Organic Transformations

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