2H‐Azirines: Recent Progress in Synthesis and Applications

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(11)

Опубликована: Янв. 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.

Язык: Английский

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Organic Chemistry in Russian Universities. Achievements of Recent Years

Russian Journal of Organic Chemistry, Год журнала: 2024, Номер 60(8), С. 1361 - 1584

Опубликована: Авг. 1, 2024

Язык: Английский

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Divergent Diazo Approach toward Alkyl 5/4-Hydroxy-3H-benzo[e]indole-4/5-carboxylates

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(18), С. 13191 - 13204

Опубликована: Сен. 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.

Язык: Английский

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Acridine–Isoxazole and Acridine–Azirine Hybrids: Synthesis, Photochemical Transformations in the UV/Visible Radiation Boundary Region, and Anticancer Activity

Molecules, Год журнала: 2024, Номер 29(7), С. 1538 - 1538

Опубликована: Март 29, 2024

Easy-to-handle

Язык: Английский

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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

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Фев. 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.

Язык: Английский

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

Tetrahedron, Год журнала: 2024, Номер 167, С. 134255 - 134255

Опубликована: Сен. 6, 2024

Язык: Английский

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Organic Chemistry in Russian Universities: Achievements of recent years

Журнал органической химии, Год журнала: 2024, Номер 60(2-3)

Опубликована: Дек. 27, 2024

Язык: Английский

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

Progress in heterocyclic chemistry, Год журнала: 2023, Номер unknown, С. 281 - 332

Опубликована: Янв. 1, 2023

Язык: Английский

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