Transition metal-catalysed carbene- and nitrene transfer to carbon monoxide and isocyanides

Chemical Society Reviews, Год журнала: 2022, Номер 51(14), С. 5842 - 5877

Опубликована: Янв. 1, 2022

Transition metal-catalysed carbene- and nitrene transfer to the C1-building blocks carbon monoxide isocyanides provides heteroallenes (i.e. ketenes, isocyanates, ketenimines carbodiimides). These are versatile reactive compounds allowing in situ transformation towards numerous functional groups organic compounds, including heterocycles. Both one-pot tandem processes have been developed providing valuable synthetic methods for chemistry toolbox. This review discusses all known transition reactions of hereby obtained, with a special focus on general mechanistic considerations.

Язык: Английский

---

Recent Advances in Domino Synthesis of Fused Polycyclic N‐Heterocycles Based on Intramolecular Alkyne Hydroamination under Copper Catalysis

Chinese Journal of Chemistry, Год журнала: 2023, Номер 41(24), С. 3751 - 3771

Опубликована: Сен. 4, 2023

Comprehensive Summary Fused polycyclic N ‐heterocycles are very important scaffolds in biomedicinal chemistry and materials science. Intramolecular alkyne hydroamination is a powerful method for the construction of ‐heterocycles. In last two decades, copper‐catalyzed domino reactions based on intramolecular has emerged as robust strategy assembling various fused Great progress been achieved this area. This short review covers advances made synthesis from 2008 to 2023, will hopefully serve an inspiration towards exploration new versions transformation. The transformations introduced discussed five aspects according different key processes involved these reactions.

Язык: Английский

---

Synthesis of Imidazo[1,2-a]pyridine-Fused 1,3-Benzodiazepine Derivatives with Anticancer Activity via a One-Pot Cascade GBB-3CR/Pd(II)-Catalyzed Azide-Isocyanide Coupling/Cyclization Process

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(18), С. 13125 - 13134

Опубликована: Авг. 24, 2023

A new one-pot synthesis of imidazo[1,2-a]pyridine-fused 1,3-benzodiazepine derivatives via a sequential GBB-3CR/Pd(II)-catalyzed azide-isocyanide coupling/cyclization process was developed. The Groebke–Blackburn–Bienaymé three-component reactions (GBB-3CR) 2-aminopyridine, 2-azidobenzaldehydes, and isocyanides in the presence catalytic amount p-toluenesulfonic acid gave azide intermediates without separation. reaction followed by using another molecule to produce good yields Pd(II)-catalyzed reaction. synthetic approach produces novel nitrogen-fused polycyclic heterocycles under mild conditions. preliminary biological evaluation demonstrated that compound 6a inhibited glioma cells efficiently, suggesting potentially broad applications for medicinal chemistry.

Язык: Английский

---

Nitrene-transfer from azides to isocyanides: Unveiling its versatility as a promising building block for the synthesis of bioactive heterocycles

iScience, Год журнала: 2024, Номер 27(4), С. 109311 - 109311

Опубликована: Фев. 23, 2024

Cross-coupling azide and isocyanide have recently gained recognition as ideal methods for efficiently synthesizing asymmetric carbodiimides. This reaction exhibits high rates, efficiency, favorable atom/step/redox economy. It enables the nitrene-transfer process, facilitating formation of C-N bonds providing a direct cost-effective synthetic strategy generating diverse These carbodiimides are highly reactive compounds that can undergo

Язык: Английский

---

Cooperation between Cu+ and Cu2+ species in CuCoAl layered double hydroxide and substrate promoting effect afford a really simple protocol for the efficient synthesis of quinazolines

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(22), С. 4494 - 4501

Опубликована: Янв. 1, 2024

In this study, a really simple and efficient catalytic protocol for the construction of quinazolines from alcohol diamine has been developed based on CuCoAl layered double hydroxide (CuCoAl-LDH). The CuCoAl-LDH catalyst could accelerate cascade reactions without any additives tolerate various alcohols with satisfactory yields. Cooperation between Cu

Язык: Английский

---

Tandem ring-opening and formal [3 + 2] cycloaddition of furo[2,3-d]pyrimidine-2,4-diones

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(29), С. 6028 - 6033

Опубликована: Янв. 1, 2023

The base promoted tandem annulation reaction of activated cyclic 1,3-dipolarophiles such as 2-arylidene-1,3-indanediones, 2-(o-hydroxybenzylidene)-1,3-indanediones and 3-methyleneoxindoles with functionalized furo[2,3-d]pyrimidine-2,4-diones was systematically investigated. This provided efficient synthetic protocols for complex dispiro/dispiro fused tricyclic compounds including dispiro[indene-2,3'-cyclopentane-1',5''-pyrimidines], dispiro[indoline-3,3'-cyclopentane-1',5''-pyrimidines] spiro[cyclopenta[c]indeno[1,2-b]chromene-3,5'-pyrimidines] in good yields high diastereoselectivity. believed to proceed via sequential ring-opening the furyl ring, formal [3 + 2] cycloaddition o-hydroxyphenyl group.

Язык: Английский

---

Thiolative Annulation of N-Benzyl-N-cyanopropiolamides Leading to Divergent Synthesis of Pyrroloquinazolin-1-ones and Maleimides

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Май 8, 2025

An unprecedented successive radical-promoted thiolative annulation/Pd-catalyzed C-H amination of N-benzyl-N-cyanopropiolamides to access pyrrolo[2,1-b]quinazolin-1(9H)-ones in a one-pot manner is described. Moreover, altering the step with oxidation (reagent switch) offered maleimides from same set readily accessible precursors. Both transformations display versatility across wide range substrates, enabling efficient various functionalized quinazolin-1-ones and good yields.

Язык: Английский

---

Cobalt-Catalyzed Cascade Synthesis of 5-Amino-1,2,4-triazolo[1,5-c]quinazoline Derivatives via Multiple C–N Bonds Construction

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Май 28, 2025

A cobalt-catalyzed three-component cascade reaction for the synthesis of functionalized 5-amino-1,2,4-triazolo[1,5-c]quinazoline derivatives is presented. The involves ortho-cyanoaryl isocyanides, azides, and hydrazides, giving products in good to excellent yields. protocol highly scalable, as demonstrated by a gram-scale bioactive CGS-15943, providing robust, efficient method synthesizing triazoloquinazoline offering significant potential drug discovery further modifications.

Язык: Английский

---

Transition‐Metal‐Catalyzed Cross‐Coupling and Sequential Reactions of Azides with Isocyanides

Advanced Synthesis & Catalysis, Год журнала: 2021, Номер 363(24), С. 5344 - 5359

Опубликована: Ноя. 23, 2021

Abstract Transition‐metal‐catalyzed cross‐coupling reaction of azides with isocyanides, as a new type nitrene transformation, has become an expeditious method to prepare carbodiimides. Considering the compatibility this coupling process other systems, transition‐metal‐catalyzed sequential reactions have more popular in recent years. These remarkable advances not only involve many interesting processes, but also provide useful strategies for construction nitrogen‐containing structures, such guanidines, amidines, isoureas, and heterocyclic compounds. This review will present comprehensive picture development isocyanides their applications preparation Catalytic followed by nucleophilic additions be briefly introduced here. Most catalytic cascade involving highlighted make up main part review. magnified image

Язык: Английский

---

NaN(SiMe₃)₂/CsTFA Copromoted Aminobenzylation/Cyclization of 2-Isocyanobenzaldehydes with Toluene Derivatives or Benzyl Compounds: One-Pot Access to Dihydroquinazolines and Quinazolines

The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(5), С. 3156 - 3166

Опубликована: Фев. 14, 2022

A NaN(SiMe3)2/CsTFA copromoted aminobenzylation/cyclization reaction of 2-isocyanobenzaldehydes with toluene derivatives or benzyl compounds has been developed. The works a broad range and compounds, provides simple efficient strategy for the synthesis 4-benzyl-substitued dihydroquinazoline quinazoline from easily available acyclic starting materials in single step. Further applications, including quinazoline, dihydroindolo[1,2-c]quinazoline, dihydro-8H-isoquinolino[2,3-c]quinazoline, demonstrated tremendous potential tandem reaction.

Язык: Английский

---