The Construction of Nitrogen‐Containing Heterocycles from Alkynyl Imines

Advanced Synthesis & Catalysis, Год журнала: 2020, Номер 363(4), С. 906 - 923

Опубликована: Дек. 25, 2020

Abstract Nitrogen‐containing heterocycles have attracted considerable attention due to their extensive applications in the fields of organic synthesis, pharmaceuticals, agrochemicals, and materials science. This review focuses on recent advances synthesis nitrogen‐containing via cyclization alkynyl imines. By using this protocol, a variety heterocycles, mainly including four‐, five‐, six‐, seven‐membered aza‐spirocycles, fused aza‐heterocycles, could be obtained efficiently under mild conditions. Additionally, mechanistic features these transformations are also discussed. magnified image

Язык: Английский

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Synthesis of polysubstituted pyrrolesviaisocyanide-based multicomponent reactions as an efficient synthesis tool

New Journal of Chemistry, Год журнала: 2021, Номер 45(47), С. 21967 - 22011

Опубликована: Янв. 1, 2021

The present review covers all synthetic methods based on isocyanide-based multicomponent reactions for the preparation of polysubstituted pyrroles as parent cores many essential drugs, biologically active compounds, and compounds with wide application in materials science.

Язык: Английский

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Palladium-catalyzed cyclization of 1-alkynyl-8-iodonaphthalene and double isocyanides for the synthesis of acenaphtho[1,2-b]pyrroles

Chinese Chemical Letters, Год журнала: 2022, Номер 33(11), С. 4870 - 4873

Опубликована: Фев. 18, 2022

Язык: Английский

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Reactions Involving Multiple Isocyanide Insertions

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(7), С. 926 - 947

Опубликована: Фев. 2, 2023

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

Язык: Английский

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The new synthesis of pyrrole-fused dibenzo[b,f][1,4]oxazepine/thiazepines by the pseudo-Joullié–Ugi reactionviaan unexpected route with high chemoselectivity

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(19), С. 4095 - 4108

Опубликована: Янв. 1, 2023

A novel and unexpected route for synthesizing pyrrole-fused dibenzoxazepines/thiazepines has been designed based on a modified Ugi reaction of cyclic imines with isocyanides acetylenedicarboxylates under catalyst-free conditions. Mechanism investigation indicates that this process is carried out through the production zwitterion species (Huisgen's 1,4-dipole), which key intermediate in chemoselectivity products. This Huisgen's 1,4-dipole trapped situ variety are synthesized simple one-pot operation high yields chemoselectivity. strategy opens new reactions (pseudo-Joullié-Ugi reaction) synthesis heterocycles as special pharmaceutical scaffolds.

Язык: Английский

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Visible-light-induced radical isocyanide insertion protocol for the synthesis of difluoromethylated spiro[indole-3,3′-quinoline] derivatives

Chemical Communications, Год журнала: 2020, Номер 56(96), С. 15212 - 15215

Опубликована: Янв. 1, 2020

A protocol for visible-light-induced radical isocyanide insertion reactions the synthesis of difluoromethylated spiro[indole-3,3′-quinoline] derivatives was developed.

Язык: Английский

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Palladium-Catalyzed Imidoylation-Triggered [2 + 2 + 1] Cyclization of Internal Alkyne with Isocyanides

Organic Letters, Год журнала: 2020, Номер 22(15), С. 5931 - 5935

Опубликована: Июль 14, 2020

In this work, a palladium-catalyzed [2 + 2 1] cyclization of internal alkynes with double isocyanides is described. This facile procedure efficient for synthesizing various pyrrolo[3,2-c]quinolin-2-amines. The reaction worked well broad scope. the process, it believed that sequential isocyanide insertion, 6-exo-dig alkyne, and addition an imino group are involved.

Язык: Английский

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Synthesis of trifluoromethyl or trifluoroacetyl substituted heterocyclic compounds from trifluoromethyl‐α,β‐ynones

Journal of the Chinese Chemical Society, Год журнала: 2022, Номер 69(4), С. 594 - 603

Опубликована: Фев. 28, 2022

Abstract Recent advances in the synthesis of trifluoromethyl or trifluoroacetyl substituted heterocyclic compounds by use trifluoromethyl‐α,β‐ynones are summarized. Seven approaches will be reviewed and divided into (a) trifluoromethyl‐pyridines, trifluoromethyl‐quinolines, trifluoroacetyl‐quinolines; (b) trifluoromethyl‐oxazinopyridines trifluoromethyl‐oxazinoquinolines; (c) trifluoromethyl‐pyrazoles, trifluoromethyl‐isoxazoles, trifluoromethyl‐pyrazolo[1,5 ‐a ]pyridines; (d) trifluoromethyl‐pyrroles, trifluoromethyl‐thiophenes, trifluoromethyl‐dihydrofurans, trifluoromethyl‐isochromanone; (e) trifluoromethyl‐pyrimidines, (f) trifluoroacetyl‐1,2,3‐triazoles; (g) trifluoromethyl‐aziridines trifluoromethyl‐[1,4]diazepines.

Язык: Английский

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

Advanced Synthesis & Catalysis, Год журнала: 2021, Номер 363(11), С. 2762 - 2766

Опубликована: Март 31, 2021

Abstract A palladium‐catalysed tandem cyclisation reaction of amidoximes, isocyanides and amines to produce 5‐aminoimidazoles was developed. Various were prepared in good excellent yields under mild conditions. This elegant domino process involves the effective cleavage N−O bond formation new C−C C−N bonds a single operation. magnified image

Язык: Английский

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

ChemistrySelect, Год журнала: 2023, Номер 8(6)

Опубликована: Фев. 8, 2023

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

Язык: Английский

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