Diazo‐Based Construction of Heterocyclic Systems Via a X−H Insertion/Cyclization Cascade DOI Open Access
Ksenia Malkova, Dmitry Dar’in

European Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Окт. 30, 2024

Abstract The X−H insertion reaction (X=heteroatom) of diazo compounds has emerged as an eminent and reliant approach for the construction C−X bonds. By merging with sequential ring‐closing transformations, diverse heterocyclic systems can be obtained in a step‐economical manner. In recent years, insertion/cyclization cascades one‐pot transformations attract more research attention, especially area asymmetric synthesis. Concentrating on assembly N,O,S‐heterocycles, this Concept elucidates various combinations reactions cyclization via addition to multiple ring‐forming strategies reviewed comprise Michael‐type Conia‐ene reactions, aldol condensation, Mannich reaction.

Язык: Английский

C–H activation-initiated spiroannulation reactions and their applications in the synthesis of spirocyclic compounds DOI

Qianting Zhou,

Bin Li, Xinying Zhang

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(12), С. 2324 - 2338

Опубликована: Янв. 1, 2024

This review summarizes the most recent progress made in C–H bond activation-initiated spiroannulation reactions and their applications construction of structurally diverse biologically valuable spirocyclic scaffolds.

Язык: Английский

Процитировано

22

Synthesis of Benzoisochromene Derivatives via C–H Activation-Initiated Cascade Formal [4+2] and [2+4] Annulation of Aryl Enaminone with Vinyl-1,3-dioxolan-2-one DOI

Chun Xia Yang,

Bin Li, Peng Shi

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 19, 2025

Cascade annulation reactions can assemble structurally intricate polycyclic molecules from simple starting materials with enhanced efficiency and minimized production of waste. Presented herein is a concise effective synthesis benzoisochromene derivatives based on C-H activation-initiated cascade formal [4+2]/[2+4] aryl enaminone vinyl-1,3-dioxolan-2-one. In constructing the six-membered carbocycle, acted as C4 synthon while vinyl-1,3-dioxolan-2-one C2 synthon. O-heterocycle, other hand, former latter C3O1 To our knowledge, this first simultaneous construction both carbocycle an O-heterocycle via concurrent C-H/C-N/C-O bond cleavage C-C/C-C/C-O formation. general, novel protocol features use readily obtainable substrates broad scope, excellent atom- step-economy, intriguing reaction pathway, valuable products.

Язык: Английский

Процитировано

3

Synthesis of Heptacyclic Compounds through C–H Bond Activation-Initiated Cascade Reactions DOI
Xing He,

Kangli Liu,

Shengnan Yan

и другие.

Organic Letters, Год журнала: 2024, Номер 26(35), С. 7425 - 7430

Опубликована: Авг. 22, 2024

Presented herein is an atom- and step-economical method enabling the precise assembly of a heptacyclic scaffold containing both azocine indoline units through cascade reactions indolin-1-yl(aryl)methanimines with diazo indanediones. The formation products involves C–H bond activation double carbene insertion followed by intramolecular condensation, retro-[2 + 2] cycloaddition, recyclization. This reaction not only provided concise straightforward strategy for synthesis otherwise difficult to obtain compounds from readily available substrates but also disclosed unprecedented mode derivatives compounds. In general, this novel synthetic protocol has advantages, such as easily obtainable substrates, structurally sophisticated products, procedure, good compatibility diverse functional groups, ready scalability. Moreover, thus obtained showed decent antiproliferative activity against three human cancer cell lines.

Язык: Английский

Процитировано

9

Synthesis of Naphtho[1′,2′:4,5]furo[3,2-b]pyridinones via Ir(III)-Catalyzed C6/C5 Dual C–H Functionalization of N-Pyridyl-2-pyridones with Diazonaphthalen-2(1H)-ones DOI
Yuanshuang Xu,

Yujing Xiao,

Xinying Zhang

и другие.

Organic Letters, Год журнала: 2024, Номер 26(4), С. 786 - 791

Опубликована: Янв. 22, 2024

Presented herein is an unprecedented synthesis of naphtho[1′,2′:4,5]furo[3,2-b]pyridinones via Ir(III)-catalyzed C6/C5 dual C–H functionalization N-pyridyl-2-pyridones with diazonaphthalen-2(1H)-ones. This protocol forms C–C and C–O bonds in one pot which diazonaphthalen-2(1H)-ones serve as bifunctional reagents, providing both alkyl aryloxy sources. To the best our knowledge, this first example title compounds by using substrates. Notably, method features operational simplicity, good functional group tolerance, high efficiency, atom economy.

Язык: Английский

Процитировано

8

Synthesis of CF3-Substituted N-Heterocyclic Compounds Based on C–H Activation-Initiated Formal [2 + 3] Annulation Featuring with a Latent Nucleophilic Site DOI

Manqing Wang,

Shengnan Yan,

Bin Li

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(11), С. 7828 - 7842

Опубликована: Май 22, 2024

Presented herein is a novel synthesis of CF

Язык: Английский

Процитировано

6

Divergent synthesis of pyrrolizine derivatives through C−H bond functionalization of pyrroles DOI

Manqing Wang,

Yuanshuang Xu,

Huihang Hou

и другие.

Chemical Communications, Год журнала: 2024, Номер 60(51), С. 6536 - 6539

Опубликована: Янв. 1, 2024

Presented herein is the synthesis of diversely functionalized pyrrolizines from reaction

Язык: Английский

Процитировано

5

Ru(ii)-catalyzed regioselective [4 + 1] redox-neutral spirocyclization of aryl amidines with diazopyrazolones: direct access to spiro[indole-3,4′-pyrazol]-5′-ones DOI
Bo Cui,

Jian Shen,

Yadong Feng

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(6), С. 1811 - 1816

Опубликована: Янв. 1, 2024

An efficient protocol to construct spiro[indole-3,4′-pyrazol]-5′-ones via ruthenium( ii )-catalyzed selective C–H bond activation/[4 + 1] spirocyclization starting from easily available N -aryl amidines and diazopyrazolones has been developed.

Язык: Английский

Процитировано

4

One-Pot Synthesis of Indolin-3-ones Mediated by LiN(SiMe3)2/CsF DOI
Ruyuan Ma, Yuanyun Gu, Yan‐En Wang

и другие.

Organic Letters, Год журнала: 2024, Номер 26(24), С. 5082 - 5086

Опубликована: Июнь 7, 2024

Indolin-3-ones are essential heterocycles with wide-ranging biological activities and medicinal values, therefore, efficient approaches to their synthesis remain in demand. Herein, a novel operationally simple method generate indolin-3-ones is reported by using tandem reaction of N-methylbenzylamines methyl 2-fluorobenzoates mediated the LiN(SiMe3)2 CsF system (34 examples, 30–85% yields). The C2-quaternary indolin-3-one further demonstrated potential practicability these reactions.

Язык: Английский

Процитировано

3

Synthesis of C2-Spiroindolines Based on the Cascade Reaction of 2-Aryl-3H-indoles with Cyclopropanols DOI

Xueying Yang,

Yuanshuang Xu, Xinying Zhang

и другие.

Chinese Journal of Organic Chemistry, Год журнала: 2025, Номер 45(2), С. 694 - 694

Опубликована: Янв. 1, 2025

Язык: Английский

Процитировано

0

Synthesis of 3,6-Dihydro-2H-thiopyrans from α-Diazo-β-diketones and Vinylthiiranes via [5 + 1] Annulation DOI

Yinqiao Wang,

Jiaxi Xu

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

Опубликована: Май 17, 2025

Functionalized 3,6-dihydro-2H-thiopyrans are synthesized in moderate to good yields from α-diazo-β-diketones and vinylthiiranes under Cu(hfacac)2 catalysis microwave irradiation via [5 + 1] annulation. The reaction mechanism includes a tandem sequence of the Cu-carbenoid generation α-diazo-β-diketones, nucleophilic attack carbenoids, subsequent [2,3]-sigmatropic rearrangement. process is carbene-induced ring expansion vinylthiiranes.

Язык: Английский

Процитировано

0