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Superbase-promoted multi-molecular acetylene/arylamine self-organization to 1-arylpyrroles

Elena Yur'evna Schmidt 1, 2
Elena Yur'evna Schmidt
, 
Nadezhda Victorovna Semenova 1
Nadezhda Victorovna Semenova
, 
Elena V Ivanova 1
Elena V Ivanova
, 
Ivan A. Bidusenko 1
Ivan A. Bidusenko
, 
Boris Aleksandrovich Trofimov 1
Boris Aleksandrovich Trofimov
10.1016/j.mencom.2020.01.036
Published 2019-12-30
Communication , Volume 30, Issue 1, 109-111
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Schmidt E. Y. et al. Superbase-promoted multi-molecular acetylene/arylamine self-organization to 1-arylpyrroles // Mendeleev Communications. 2019. Vol. 30. No. 1. pp. 109-111.
GOST all authors (up to 50) Copy
Schmidt E. Y., Semenova N. V., Ivanova E. V., Bidusenko I. A., Trofimov B. A. Superbase-promoted multi-molecular acetylene/arylamine self-organization to 1-arylpyrroles // Mendeleev Communications. 2019. Vol. 30. No. 1. pp. 109-111.
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TY - JOUR
DO - 10.1016/j.mencom.2020.01.036
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.01.036
TI - Superbase-promoted multi-molecular acetylene/arylamine self-organization to 1-arylpyrroles
T2 - Mendeleev Communications
AU - Schmidt, Elena Yur'evna
AU - Semenova, Nadezhda Victorovna
AU - Ivanova, Elena V
AU - Bidusenko, Ivan A.
AU - Trofimov, Boris Aleksandrovich
PY - 2019
DA - 2019/12/30
PB - Mendeleev Communications
SP - 109-111
IS - 1
VL - 30
ER -
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@article{2019_Schmidt,
author = {Elena Yur'evna Schmidt and Nadezhda Victorovna Semenova and Elena V Ivanova and Ivan A. Bidusenko and Boris Aleksandrovich Trofimov},
title = {Superbase-promoted multi-molecular acetylene/arylamine self-organization to 1-arylpyrroles},
journal = {Mendeleev Communications},
year = {2019},
volume = {30},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.01.036},
number = {1},
pages = {109--111},
doi = {10.1016/j.mencom.2020.01.036}
}
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Schmidt, Elena Yur'evna, et al. “Superbase-promoted multi-molecular acetylene/arylamine self-organization to 1-arylpyrroles.” Mendeleev Communications, vol. 30, no. 1, Dec. 2019, pp. 109-111. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.01.036.

Keywords

Acetylene
arylamines
ethynylation.
imines
pyrroles
superbases
vinylation

Abstract

A new superbase-promoted reaction of acetylene involves self-organization of its three molecules with one molecule of arylamine in KOH/DMSO system to afford 1-aryl-2,5- dimethylpyrroles in up to 63% yields. The key step of this reaction cascade is assumed to be the nucleophilic addition of acetylene to the C=N bond of the intermediate aldimine (aza-Favorsky reaction).

References

5.
Vereshchagin A.N., Elinson M.N., Anisina Y.E., Ryzhkov F.V., Goloveshkin A.S., Bushmarinov I.S., Zlotin S.G., Egorov M.P.
Mendeleev Communications, 2015
6.
Calcium Carbide: A Unique Reagent for Organic Synthesis and Nanotechnology
Rodygin K.S., Werner G., Kucherov F.A., Ananikov V.P.
Chemistry - An Asian Journal, 2016
7.
Acetylene in Organic Synthesis: Recent Progress and New Uses
Voronin V.V., Ledovskaya M.S., Bogachenkov A.S., Rodygin K.S., Ananikov V.P.
Molecules, 2018
8.
Alkyne Origami: Folding Oligoalkynes into Polyaromatics.
Alabugin I.V., Gonzalez-Rodriguez E.
Accounts of Chemical Research, 2018
9.
Alkynes as Privileged Synthons in Selected Organic Name Reactions.
Heravi M.M., Dehghani M., Zadsirjan V., Ghanbarian M.
Current Organic Synthesis, 2019
10.
Gold as a catalyst. Part II. Alkynes in the reactions of carbon - Carbon bond formation
Alyabyev S.B., Beletskaya I.P.
Russian Chemical Reviews, 2018
11.
Production of calcium carbide from fine biochars.
Li G., Liu Q., Liu Z., Zhang Z.C., Li C., Wu W.
Angewandte Chemie - International Edition, 2010
13.
Catalytic reactions of acetylene: a feedstock for the chemical industry revisited.
Trotuş I., Zimmermann T., Schüth F.
Chemical Reviews, 2013
14.
Acidities of water and simple alcohols in dimethyl sulfoxide solution
Olmstead W.N., Margolin Z., Bordwell F.G.
Journal of Organic Chemistry, 1980
15.
Dimethyl Sulfoxide/Potassium Hydroxide: A Superbase for the Transition Metal‐Free Preparation of Cross‐Coupling Products
Yuan Y., Thomé I., Kim S.H., Chen D., Beyer A., Bonnamour J., Zuidema E., Chang S., Bolm C.
Advanced Synthesis and Catalysis, 2010
16.
Acetylenes in the Superbase-Promoted Assembly of Carbocycles and Heterocycles
Trofimov B.A., Schmidt E.Y.
Accounts of Chemical Research, 2018
17.
One-Pot Assembly of 7-Methylene-6,8-dioxabicyclo[3.2.1]octanes, Congeners of Frontalin, from Ketones and Acetylene
Trofimov B.A., Schmidt E.Y., Ushakov I.A., Mikhaleva A.I., Zorina N.V., Protsuk N.I., Senotrusova E.Y., Skital'tseva E.V., Kazheva O.N., Alexandrov G.G., Dyachenko O.A.
European Journal of Organic Chemistry, 2009
18.
Base-Catalyzed Domino Cyclization of Acetylenes with Ketones to Functionalized Cyclopentenes
Schmidt E.Y., Trofimov B.A., Bidusenko I.A., Cherimichkina N.A., Ushakov I.A., Protzuk N.I., Gatilov Y.V.
Organic Letters, 2014
19.
Furans Conjugated with Bulky Aromatic Systems: One‐Pot Synthesis from Ketones and Acetylene
Schmidt E.Y., Bidusenko I.A., Cherimichkina N.A., Ushakov I.A., Borodina T.N., Smirnov V.I., Trofimov B.A.
Chemistry - A European Journal, 2015
20.
One-pot assembly of 4-methylene-3-oxa-1-azabicyclo[3.1.0]hexanes from alkyl aryl(hetaryl) ketoximes, acetylene, and aliphatic ketones: a new three-component reaction
Trofimov B.A., Schmidt E.Y., Mikhaleva A.I., Ushakov I.A., Protsuk N.I., Senotrusova E.Y., Kazheva O.N., Aleksandrov G.G., Dyachenko O.A.
Tetrahedron Letters, 2009
21.
Transition-Metal-Free Addition of Acetylenes to Ketimines: the First Base-Catalyzed Ethynylation of the C=N Bond
Bidusenko I.A., Schmidt E.Y., Ushakov I.A., Trofimov B.A.
European Journal of Organic Chemistry, 2018
22.
10.1016/j.mencom.2020.01.036_sbref0055a
Trofimov
Zh. Org. Khim., 1979
23.
10.1016/j.mencom.2020.01.036_sbref0055b
Trofimov
Zh. Org. Khim., 1976
24.
Eine neue Pyrrolsynthese aus Butadiin‐Derivaten
Schulte K.E., Reisch J., Walker H.
Chemische Berichte, 1965