Synthesis of heterocyclic compounds through nucleophilic phosphine catalysis

Huang, Yehui; Liao, Jianning; Wang, Wei; Liu, Honglei; Guo, Hongchao

doi:10.1039/d0cc05699e

Cited by 117 publications

(37 citation statements)

References 387 publications

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“…Heterocyclizations are powerful tools for the synthesis of five-membered heterocycles − that are often found in natural products , and synthetic pharmaceuticals − and widely used in material science and organic synthesis. − Recent studies revealed that oxidative heterocyclizations − could evoke novel and useful catalytic transformations, which otherwise are difficult to achieve. For example, the cyclization of ketene dithioacetals, − a kind of electron-rich olefin, under electrochemical conditions afforded the cyclic amino acid derivatives (Scheme a, X = NH) .…”

mentioning

confidence: 99%

Visible-Light-Induced Formation of Thiavinyl 1,3-Dipoles: A Metal-Free [3+2] Oxidative Cyclization with Alkynes as Easy Access to Thiophenes

Zheng

Song

et al. 2021

Org. Lett.

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A visible-light-induced [3+2] oxidative cyclization of various alkynes with easily available ketene dithioacetals as the previously unknown thiavinyl 1,3-dipoles in the presence of an acridine photosensitizer is reported. A series of multisubstituted thiophenes were achieved regioselectively in ≤98% yields under very mild metal-free conditions without other additives. This reaction could tolerate a wide range of substrates and achieve good efficiency in large-scale syntheses. The reaction mechanism and their applications are described in detail to reveal the reactivity of the new 1,3-dipoles and the selectivity of the reactions.

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confidence: 99%

Visible-Light-Induced Formation of Thiavinyl 1,3-Dipoles: A Metal-Free [3+2] Oxidative Cyclization with Alkynes as Easy Access to Thiophenes

Zheng

Song

et al. 2021

Org. Lett.

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“…The compounds ( Fig. 1 ) 3-(4,5-dinitro-imidazol-1-yl)prop-2-yn-1-amine (1), 2-chloro-N-[3-(4,5-dinitro-imidazol-1-yl)prop-2-ynyl]acetamide (2), N-[3-(2-methyl-4,5-dinitro-imida-zol-1-yl)prop-2-ynyl]-3-phenyl-oxiran-2-amine (3), 1-[3-[(3-phenyloxiran-2-yl)amino] prop-1-ynyl]imidazole-4,5-diamine (4) and 3-[3-[(3-phenyloxiran-2-yl)amino]prop-1-ynyl]-4,6,7,9-tetrahydroimidazo[4,5-b] 1 4 diazocine-5,8-dione (5) were prepared using a previously reported method 11 . The other reagents were acquired from Sigma-Aldrich Co.…”

Section: Methodsmentioning

confidence: 99%

Evaluation of Biological Activity of a Diazocine Derivative against Heart Failure Using an Ischemia-Reperfusion Injury Model

et al. 2022

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Background There are studies, which suggest that some diazocine derivatives can exert effects on the cardiovascular system; however, these effects are not very clear. Objective The aim of this research was to evaluate the biological activity of a diazocine derivative against heart failure translated as area infarct. Methods Biological activity produced by diazocine derivatives against heart failure was determinate using an ischemia/reperfusion injury model. Besides, to characterize the molecular mechanism of effect exerted by diazocine derivative on left ventricular pressure (LVP) was determinate in an isolated rat heart model using nifedipine, PINAME TXA2, and quinalizarin as controls. Results The results showed that diazocine derivative decrease the infarct area and increase the LVP. However, the effect produced by diazocine derivative on LVP was inhibited in the presence of quinalizarin. Conclusions The results indicate that biological activity produced by diazocine derivative on left ventricular pressure is through protein CK2 activation; this phenomenon could be translated as a decrease in both infarct area and heart failure.

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“…As far as their utilization in synthesis is concerned, it has been limited to very few examples. In the cases reported to date, [ 25 ] the dienophile counterparts were limited to dimethyl acetylenedicarboxylate and acetylenedicarboxylic acid. The conditions used for their synthesis have generally led, in modest yields, to mixtures of stereoisomers and regioisomers (pincer vs. domino).…”

Section: Introductionmentioning

confidence: 99%

A density functional theory study of the reactions of furans with substituted alkynes to form oxanorbornadienes and subsequent [4 + 2] and [2 + 2 + 2] addition reactions

Samba

Tia

Adei

2021

J of Physical Organic Chem

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This work investigated theoretically, at the M06/6‐311++G(d,p) level of theory, the Diels–Alder reactions of furan with substituted alkynes to afford oxanorbornadienes and the subsequent [4 + 2] and [2 + 2 + 2] cycloaddition reactions leading to the formation of heterocyclic furans, deltacyclenes, and bicyclic oxanorbornadienes, which have high utility in the chemical and pharmaceutical industries. The results show that in the initial Diels–Alder reactions to afford oxanorbornadiene intermediates, reactions of alkynes bearing electron‐withdrawing substituents have lower activation barriers compared with those with electron‐donating substituents. In the [4 + 2] reactions of the oxanorbornadiene intermediates to form bicyclic oxanorbornadienes, oxanorbornadienes with electron‐donating groups favor addition across the unsubstituted olefinic bond, whereas those with electron‐withdrawing substituents favor addition across the substituted double bond, but in both cases, the exo stereoisomer is favored. The regioselectivity of the reactions are strictly dictated by the nature of substituent on oxanorbornadiene. The retrocleavage step, regardless of the addition sequence and nature of substituents, is the rate‐determining step. For the reactions of substituted oxanorbornadienes with furan along the [4 + 2] cycloaddition and the [2 + 2 + 2] cycloaddition (dimerization) of substituted oxanorbornadienes, we observed a decrease in activation barriers when electron‐withdrawing substituents are involved. The global electrophilicity indices (ω) and maximum electronic charge transfer (ΔNmax) computed for various oxanorbornadiene derivatives considered in this work is consistent with energetic trends and experimental outcomes. Perturbation molecular orbital theory was employed to rationalize the results.

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Synthesis of heterocyclic compounds through nucleophilic phosphine catalysis

Abstract: Nucleophilic phosphine catalysis is a practical and powerful synthetic tool for the synthesis of various heterocyclic compounds with the advantages of environmental-friendly, metal-free, and mild reaction conditions. The present report...

Cited by 117 publications

References 387 publications

Visible-Light-Induced Formation of Thiavinyl 1,3-Dipoles: A Metal-Free [3+2] Oxidative Cyclization with Alkynes as Easy Access to Thiophenes

Visible-Light-Induced Formation of Thiavinyl 1,3-Dipoles: A Metal-Free [3+2] Oxidative Cyclization with Alkynes as Easy Access to Thiophenes

Evaluation of Biological Activity of a Diazocine Derivative against Heart Failure Using an Ischemia-Reperfusion Injury Model

A density functional theory study of the reactions of furans with substituted alkynes to form oxanorbornadienes and subsequent [4 + 2] and [2 + 2 + 2] addition reactions

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