Assembly of 5‐Aminoimidazoles via Palladium‐Catalysed Double Isocyanide Insertion Reaction

Xu, Weiqing; Fu, Jinping; Mo, Jia-Hui; Tian, Yuhong; Liu, Chun-You; Tang, Hai‐Tao; Sun, Zijun; Pan, Ying‐Ming

doi:10.1002/adsc.202100142

Cited by 15 publications

(4 citation statements)

References 38 publications

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“…In 2021, Pan et al synthesized 5-aminoimidazoles 135 in moderate to high yields (57-91%) from the reaction of amidoximes 129, amines 130 and isocyanides 2 in the presence of Pd(OAc) 2 and PPh 3 in DMSO at 100 °C (Scheme 18). [35] Control experiments showed that this process started by oxidative addition of amidoximes 129 into Pd(0)L 2 (produced from the reaction of PdL 2 and PPh 3 ) to produce the palladium species 131. Then, the double insertion of two molecules of isocyanides 2 into intermediates 131 gave intermediates 132.…”

Section: Amidoximesmentioning

confidence: 99%

Reactions Involving Multiple Isocyanide Insertions

Tashrifi

mohammadi-khanaposhtani

Gholami

et al. 2023

Adv Synth Catal

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Isocyanides (isonitriles or carbylamine) have been intensively used in organic synthesis to prepare a diverse variety of N‐heterocycles on the basis of the carbene‐like reactivity of their divalent carbon atom. Isocyanides participate in a variety of reactions involving one, two, or more isocyanides. Compared to the popularity of single isocyanide reactions, few examples of reactions involving two or more isocyanides have been reported. In this review, we categorized and classified the literatures of reactions involving two or more isocyanides especially double isocyanide insertions under metal‐catalyzed or metal‐free conditions from 2014 to 2022.

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Section: Amidoximesmentioning

confidence: 99%

Reactions Involving Multiple Isocyanide Insertions

Tashrifi

mohammadi-khanaposhtani

Gholami

et al. 2023

Adv Synth Catal

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“…Pan, Sun, and co-workers reported the synthesis of 5aminoimidazole derivatives via palladium-promoted double cyanide insertion. [40] In these three-component domino reactions, amidoximes, isocyanides, and primary amines were treated with Pd(OAc) 2 and PPh 3 in DMSO to give (Z)-products 11 with medium to excellent yields (Scheme 27). These were formed in a domino process involving the cleavage of the NÀ O bond and the formation of new CÀ C and CÀ N bonds.…”

Section: Intermolecular Ring Formationsmentioning

confidence: 99%

Recent Advances in the Synthesis of Five‐membered Nitrogen Heterocycles Induced by Palladium Ions and Complexes

Molnár

2023

ChemistrySelect

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This review aims to collect and analyze recent results with respect to the use of varied palladium preparations in the synthesis of five-membered nitrogen heterocycles including condensed derivatives. Results have been selected with focus on studies of the last three years. Furthermore, a common feature of all methods treated here is that the nitrogencontaining five-membered ring is formed via ring closing of appropriate starting materials. Selected examples discussed will reveal that a plethora of products from small monocycles to condensed multi-ring systems can be successfully accessed. Major features are wide product ranges, high product yields and stereoselectivities often achieved under mild reaction conditions.

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“…Similarly, the reaction of N -sulfonyl-1,2,3-triazoles with oxadiazolone provides 5-sulfonamido-1-methyl/benzylimidazoles (Scheme 1, eqn (5)). Very recently, Wang and co-workers 54 developed an interesting synthesis method for 5-aminoimidazole derivatives via palladium-catalyzed multicomponent reactions involving amidoximes, isocyanides, and amines (Scheme 1, eqn (6)). There are currently only a few available methods for the synthesis of 5-aminoimidazoles.…”

Section: Introductionmentioning

confidence: 99%