Five-membered ring systems: with more than one N atom DOI
Larry Yet

Progress in heterocyclic chemistry, Journal Year: 2023, Volume and Issue: unknown, P. 281 - 332

Published: Jan. 1, 2023

Language: Английский

2H‐Azirines: Recent Progress in Synthesis and Applications DOI
Fen Xu,

Fan‐Wang Zeng,

Wenjie Luo

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(11)

Published: Jan. 29, 2024

Abstract 2H ‐arizines are important three‐membered heterocycles in organic chemistry. Recently, many advances the synthesis and functionalization of have been reported. Neber rearrangement, isomerization isoxazole, oxidation enamine, C−H bond activation, decomposition vinyl azide, alkyne, multi‐step developed for efficient assembly ‐azirines. As versatile highly strained unsaturated heterocycles, ‐azirines can be used as distinctive building blocks towards significant functional groups, attracted extensive attention fabrication numerous heterocycles. Recent studies focused on [3+n] ring‐expansion reactions, nucleophilic addition C=N double or continuous followed by cyclization, ring‐opening to acyclic compounds, substitution sp 3 ‐C−H One most critical challenges is seeking a selective opening specific three bonds azirine circle, some what achieved basis metal catalyst, photocatalysis, combination catalyst photocatalysis. In this review, recent involving reactivity accompanied with breakthroughs summarized. The review mainly covers period from 2019 2023.

Language: Английский

Citations

11
Organic Chemistry in Russian Universities. Achievements of Recent Years DOI
Ivan I. Stoikov, И. С. Антипин, В. А. Бурилов

et al.

Russian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 60(8), P. 1361 - 1584

Published: Aug. 1, 2024

Language: Английский

Citations

4
Divergent Diazo Approach toward Alkyl 5/4-Hydroxy-3H-benzo[e]indole-4/5-carboxylates DOI
Timur O. Zanakhov, Екатерина Е. Галенко, Михаил С. Новиков

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(18), P. 13191 - 13204

Published: Sept. 6, 2023

A divergent diazo approach toward alkyl 5/4-hydroxy-3H-benzo[e]indole-4/5-carboxylates has been developed. The reaction of 1,3-diketones with 2-diazo-3-oxo-3-(2H-azirin-2-yl)propanoates catalyzed by Co(acac)3 or Ni(acac)2 gives various 3-(1H-pyrrol-2-yl)-2-diazo-3-oxopropanoate in good yields. latter undergo Wolff rearrangement followed the 6π-cyclization transient ketene to form 5-hydroxy-3H-benzo[e]indole-4-carboxylates bearing substituents positions 1, 2, 7, and 8, as well derivatives methyl 4-hydroxy-6H-thieno[2,3-e]indole-5-carboxylates 5-hydroxy-7H-benzo[c]carbazole-6-carboxylate under thermolysis Rh2(OAc)4 catalysis. Isomeric benzoindoles, 4-hydroxy-3H-benzo[e]indole-5-carboxylates, have prepared Boc-protection pyrrole nitrogen 3-(1H-pyrrol-2-yl)-2-diazo-3-oxopropanoates an intramolecular formal carbene insertion into aromatic C–H bond Cu(OTf)2. hydroxyl group 5/4-hydroxy-3H-benzo[e]indole-4/5-carboxylates, through formation corresponding triflates, allows introduction 5/4 position benzo[e]indoles using cross-coupling even a new heterocyclic backbone, benzo[k]pyrrolo[2,3-i]phenanthridine, via tandem Suzuki reaction/nucleophilic acyl substitution.

Language: Английский

Citations

10
Acridine–Isoxazole and Acridine–Azirine Hybrids: Synthesis, Photochemical Transformations in the UV/Visible Radiation Boundary Region, and Anticancer Activity DOI Creative Commons
Екатерина Е. Галенко, Михаил С. Новиков, Alexander S. Bunev

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(7), P. 1538 - 1538

Published: March 29, 2024

Easy-to-handle

Language: Английский

Citations

3
Synthesis of Azirinyl Ethynyl Ketones and Their Use in the Preparation C(O)C≡CR-Substituted NH-Pyrroles/NH-Imidazoles and Azole–Azine/Azole–Azole Heterocyclic Hybrids DOI
Екатерина Е. Галенко, Vladimir A. Bodunov, Artur E. Taishev

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 24, 2025

Azirinyl-substituted conjugated ynones were first synthesized by the reaction of lithiated acetylenes with 2H-azirine-2-carbonyl chlorides. Azirinyl ethynyl ketones containing only a C(O)C≡CR substituent at position 2 azirine ring are good precursors for obtaining α-C(O)C≡CR substituted NH-pyrroles and 5-[C(O)C≡CR]-substituted NH-imidazoles, reacting selectively moiety 1,3-diketones arylamidines, respectively. Various N-heterocyclic hybrids (pyrrole-pyrimidine, imidazole-pyrimidine, pyrrole-isoxazole, imidazole-isoxazole, pyrimidine-pyrrole-thiophene, pyrrole-pyrimidine-thiophene, imidazole-pyrimidine-thiophene, isoxazole-pyrrole-thiophene) have been prepared based on orthogonal or domino reactions an moieties azirinyl ketones.

Language: Английский

Citations

0
Azirine Weinreb amides: preparation and use in the synthesis of 2-acylated aziridines and azirines DOI

Irina N. Prokop'eva,

Olesya A. Tomashenko,

Daria R. Matveeva

et al.

Tetrahedron, Journal Year: 2024, Volume and Issue: 167, P. 134255 - 134255

Published: Sept. 6, 2024

Language: Английский

Citations

2
Organic Chemistry in Russian Universities: Achievements of recent years DOI

Ivan I. Stoykov,

И. С. Антипин, В. А. Бурилов

et al.

Журнал органической химии, Journal Year: 2024, Volume and Issue: 60(2-3)

Published: Dec. 27, 2024

Language: Английский

Citations

0
Five-membered ring systems: with more than one N atom DOI
Larry Yet

Progress in heterocyclic chemistry, Journal Year: 2023, Volume and Issue: unknown, P. 281 - 332

Published: Jan. 1, 2023

Language: Английский

Citations

0