One-Pot Synthesis of 1,2,3-Triarylindoles through Cascade Reactions Using Calcium Carbide, Iodoarenes, and Aromatic Amines

Liu, Zhenrong; Wang, Zhiqiang; Liao, Haiyan; Li, Zheng

doi:10.1021/acs.orglett.3c02069

Cited by 16 publications

(1 citation statement)

References 35 publications

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“…Calcium carbide was chosen as a vinylating agent due to recent progress in this field and appropriate reaction set up. [12] Although the vinylation of unsaturated alcohols with CaC 2 is more complicated than that of saturated alcohols due to alkene formation as a result of undesired elimination, all the vinyl ethers were isolated in moderate and good yields.…”

Section: Vinylation Of Unsaturated Alcohols: Synthesis Of Model Compo...mentioning

confidence: 99%

Selective Hydrogenation of Unsaturated Vinyl Ethers in Two‐Chamber Gauge‐Reactor

Gyrdymova,

Saybulina,

Mironenko

et al. 2024

Asian J Org Chem

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A pressure gauge was incorporated into a two‐chamber glass H‐tube to continuously monitor the pressure inside a reactor when working with gases. The ex situ generated H2, D2, acetylene and CO2 were tested in pressure gauge reactors, and calibration curves were plotted. A series of unsaturated compounds with two or more double C=C bonds accessible for hydrogenation were synthesized for hydrogenation. The hydrogenation proceeded well due to constant pressure control, and the desired products were isolated in good yields. The same hydrogenation procedures were then carried out using steel autoclaves to verify the results and compare them. Surprisingly, almost the same results were obtained, confirming the effectiveness of self‐made glass reactors. The hydrogenation mechanism was further investigated using D‐labeled reagents. The kinetics of hydrogenation was studied both in manometric glass reactors and in steel autoclaves, which showed a similar nature of the main process in both reaction units. Thus, the created reactors can be effectively used in barometric transformations instead of steel autoclaves in appropriate cases.

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Section: Vinylation Of Unsaturated Alcohols: Synthesis Of Model Compo...mentioning

confidence: 99%

Selective Hydrogenation of Unsaturated Vinyl Ethers in Two‐Chamber Gauge‐Reactor

Gyrdymova,

Saybulina,

Mironenko

et al. 2024

Asian J Org Chem

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One‐Step Construction of 9,10‐Diarylphenanthrenes Using Solid Calcium Carbide as an Alternative of Gaseous Acetylene

Liu,

Wang,

2024

Asian J Org Chem

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A convenient method for the construction of 9,10‐diarylphenanthrenes through one‐pot multicomponent reactions of iodoarenes, o‐bromobenzoic acids, and calcium carbide is described. A series of target compounds are efficiently synthesized via Csp2−H activation and the simultaneous construction of five C−C bonds. The salient features of this method are the use of inexpensive and easy‐to‐handle solid alkyne source as an alternative of flammable and explosive gaseous acetylene. Meanwhile the use of commercially available substrates, wide functional tolerance, and simple workup procedure are also advantage of this protocol. In addition, the corresponding products can also be synthesized on gram scale.

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1,2,4‐Triazines and Calcium Carbide in the Catalyst‐Free Synthesis of 2,3,6‐Trisubstituted Pyridines and Their D‐, ¹³C‐, and Doubly D₂‐¹³C₂‐Labeled Analogues

Voronin,

Polynski,

Ledovskaya

2023

Chemistry An Asian Journal

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A novel synthetic approach to 2,3,6‐trisubstituted pyridines, their 4,5‐dideuterated derivatives, 4,5‐13C2‐ and doubly‐labeled D2‑13C2‐pyridines has been developed using catalyst‐free [4+2] cycloaddition of 1,2,4‐triazines and in situ generated acetylene or labeled acetylene. Calcium carbide and water or deuterium oxide were used for the in situ generation of acetylene and dideuteroacetylene. Calcium carbide‐13C2 in the mixture with water or deuterium oxide was applied as 13C2‐acetylene and D2‐13C2‐acetylene source.

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One-Pot Synthesis of 1,2,3-Triarylindoles through Cascade Reactions Using Calcium Carbide, Iodoarenes, and Aromatic Amines

Cited by 16 publications

References 35 publications

Selective Hydrogenation of Unsaturated Vinyl Ethers in Two‐Chamber Gauge‐Reactor

Selective Hydrogenation of Unsaturated Vinyl Ethers in Two‐Chamber Gauge‐Reactor

One‐Step Construction of 9,10‐Diarylphenanthrenes Using Solid Calcium Carbide as an Alternative of Gaseous Acetylene

1,2,4‐Triazines and Calcium Carbide in the Catalyst‐Free Synthesis of 2,3,6‐Trisubstituted Pyridines and Their D‐, ¹³C‐, and Doubly D₂‐¹³C₂‐Labeled Analogues

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One-Pot Synthesis of 1,2,3-Triarylindoles through Cascade Reactions Using Calcium Carbide, Iodoarenes, and Aromatic Amines

Cited by 16 publications

References 35 publications

Selective Hydrogenation of Unsaturated Vinyl Ethers in Two‐Chamber Gauge‐Reactor

Selective Hydrogenation of Unsaturated Vinyl Ethers in Two‐Chamber Gauge‐Reactor

One‐Step Construction of 9,10‐Diarylphenanthrenes Using Solid Calcium Carbide as an Alternative of Gaseous Acetylene

1,2,4‐Triazines and Calcium Carbide in the Catalyst‐Free Synthesis of 2,3,6‐Trisubstituted Pyridines and Their D‐, 13C‐, and Doubly D2‐13C2‐Labeled Analogues

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1,2,4‐Triazines and Calcium Carbide in the Catalyst‐Free Synthesis of 2,3,6‐Trisubstituted Pyridines and Their D‐, ¹³C‐, and Doubly D₂‐¹³C₂‐Labeled Analogues