4-Diazoisochroman-3-imines: A Class of Metal Carbene Precursors for the Synthesis of Isochromene Derivatives

Ren, Aiming; Lang, Bernard; Lin, Jialun; Lü, Ping; Wang, Yanguang

doi:10.1021/acs.joc.7b01860

Cited by 25 publications

(7 citation statements)

References 31 publications

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“…Novikov et al reported a tandem process for the synthesis of 5H-pyrazino [2,3-b] indoles (22) derivatives by using 2Hazirines (20) and 3-diazoindolin-2-imines (21) in the presence of Rh 2 (OAc) 4 as a catalyst (Scheme 7). [18] Additionally, another tandem strategy to form 5H-pyrazino [2,3-b] indole 3-carboxylates was reported in which reaction started with 5-alkoxyisoxazoles which readily converted into 2H-azirines 2-carboxylate in-situ.…”

Section: Synthesis Of N-containing Heterocyclesmentioning

confidence: 99%

“…In their next study Wang's group employed 4-diazoisochroman-3-imines (37) as a carbene precursors with alkenes (38) or conjugated dienes (40) in the presence of Rh-catalyst to furnished spiro[cyclopropane-1,4'-isochro-man]-3'-imines (39) and tetrahydroisochromeno [3,4-b] azepines (41) via a formal [2 + 1] (i. e., cyclopropanation) or [4 + 3] cycloaddition respectively (Scheme 10). [21] During this study, they screened various rhodium salts along with solvents, temperature and reaction time and found Rh 2 (HFB) 4 (1 mol %) in toluene (1 mL) at room temperature for 3 h as best reaction condition to attained highest conversion. Next, a [3 + 2] formal cycloaddition of diazo and alkynes (42) occurred under the co-catalysis of Rh(II)-salt and AgOTf and afforded the desired products i. e. 2-aryl-3,5dihydroisochromeno [3,4-b]pyrroles (43) in good yield.…”

Section: Synthesis Of N-and O-containing Heterocyclesmentioning

confidence: 99%

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Rhodium‐Catalyzed Cascade Reactions using Diazo Compounds as a Carbene Precursor to Construct Diverse Heterocycles

2021

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Diazo compounds being used as a precursor of carbenes in synthetic chemistry by reacting them in different manners like photochemically, thermally or with metal catalysts. Further, the use of metals as a catalyst generates metallocarbenes in the reaction medium which has similar reactivity like free carbenes. In this context, a number of transition metal catalysts like Rh, Pd, Cu, Ru, Ir, Fe etc. have been employed to generate metal bound carbenes in the reaction medium. Among various metal catalyst, rhodium being used extensively in industry as well as in academia to catalyze a number of cascade transformations containing carbene insertion/transfer. In this review, we are covering the efforts made in the last five years toward the synthesis of highly important heterocyclic compounds such as isoquinoline, indoles, isocoumines, oxazoles, carbazoles etc. through rhodium catalysed cascade reactions containing carbene transfer as the vital step.

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Section: Synthesis Of N-containing Heterocyclesmentioning

confidence: 99%

Section: Synthesis Of N-and O-containing Heterocyclesmentioning

confidence: 99%

Rhodium‐Catalyzed Cascade Reactions using Diazo Compounds as a Carbene Precursor to Construct Diverse Heterocycles

2021

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“…Notably, no silver salt was used in this transformation. [19] Experimental observations indicated that Rh(II)-catalyzed [2 + 1] cycloaddition between diazo compounds with dienes, which followed by heatinduced aza-Cope rearrangement, might be involved.…”

Section: Intermolecular Migrationsmentioning

confidence: 99%

“…Lee group also developed a azepinoindoles synthesis via rhodium‐catalyzed formal [4+3] cycloaddition between 3‐diazoindolin‐2‐imines and 1,3‐dienes, featuring good functional group tolerance, short reaction time. Notably, no silver salt was used in this transformation [19] . Experimental observations indicated that Rh(II)‐catalyzed [2+1] cycloaddition between diazo compounds with dienes, which followed by heat‐induced aza‐Cope rearrangement, might be involved.…”

Section: Synthesis Of Azepines Via Rhodium Catalysismentioning

confidence: 99%

Recent Achievements in the Rhodium‐Catalyzed Concise Construction of Medium N‐Heterocycles, Azepines and Azocines

Ouyang

Rao

et al. 2020

Adv Synth Catal

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Medium N-heterocycles, azepines and azocines, serve as important skeletons that occurred widely in natural products, however, due to the lack of efficient synthetic methodologies, their application potential in biologically active molecules, pharmaceuticals and agrochemicals remained to be explored. In this context, rhodium catalysis in this field featured good reactivity and functional group tolerance, with readily available starting materials, and enabled rapid access to the azepines and azocines. Delightfully, great achievements in the concise construction of these 7 and 8-membered N-heterocycles under rhodium catalysis have been made, which mainly included cycloisomerization of unsaturated CÀ X bonds (which might also combine the ring-opening strategy on strained rings), metal carbenoid or nitrene insertion involved transformations and direct CÀ H activation reactions. Considering the great performance of rhodium catalyst in the synthesis of azepines and azocines, herein, we summarized the recent results in this field, and wish to give further insight and inspired more encouraging methodologies and new drug discovery based on these 7 and 8membered N-heterocycles.

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“…On the other hand, we recently reported a new family of diazo compounds, 4-diazoisochroman-3-imines, which could be easily prepared by a copper-catalyzed alkyne–azide cycloaddition . These diazo compounds had been demonstrated to be effective to form rhodium carbenes in the presence of Rh(II) and brought out a series of Rh(II)-catalyzed reactions, such as cyclopropanation as well as formal [3 + 2] and [3 + 4] cycloadditions .…”

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confidence: 99%

Rh(III)-Catalyzed Synthesis of 3-Amino-4-arylisoquinolinones from 4-Diazoisochroman-3-imines and N-Methoxybenzamides

Chang

et al. 2019

Org. Lett.

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A Rh(III)-catalyzed reaction of N-methoxybenzamides and 4-diazoisochroman-3-imines is described. This method offers a rapid entry to 3-amino-4-arylisoquinolinone architectures from readily available starting materials under mild reaction conditions. A one-pot cascade C−H bond activation/formal [4 + 2] cycloaddition mechanism is proposed. The synthesized 3-amino-4-arylisoquinolinones can be conveniently converted into dibenzo[c,f ][1,8]naphthyridines.3-Amino-4-arylisoquinolinones are privileged structures in medicinal science (Figure 1). 1 For instance, compound I is

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4-Diazoisochroman-3-imines: A Class of Metal Carbene Precursors for the Synthesis of Isochromene Derivatives

Cited by 25 publications

References 31 publications

Rhodium‐Catalyzed Cascade Reactions using Diazo Compounds as a Carbene Precursor to Construct Diverse Heterocycles

Rhodium‐Catalyzed Cascade Reactions using Diazo Compounds as a Carbene Precursor to Construct Diverse Heterocycles

Recent Achievements in the Rhodium‐Catalyzed Concise Construction of Medium N‐Heterocycles, Azepines and Azocines

Rh(III)-Catalyzed Synthesis of 3-Amino-4-arylisoquinolinones from 4-Diazoisochroman-3-imines and N-Methoxybenzamides

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