Recent Progress in Application of Propargylic Alcohols in Organic Syntheses

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(18), P. 2991 - 3019

Published: July 14, 2023

Abstract Propargylic alcohols are readily available bifunctional (alkyne and hydroxyl groups) synthons, which recognize as one of the attractive synthetic feedstock in organic transformations. Especially, recent years employment these valuable molecules has frequently been observed literature. Hence, present review highlights advancements application propargylic cyclization, substitution, addition reactions.

Language: Английский

---

Catalytic Aminium Radical-Cation Salt (Magic Blue)-Initiated S_N2-Type Nucleophilic Ring-Opening Transformations of Aziridines

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(4), P. 2247 - 2263

Published: Feb. 7, 2024

A simple and atom economic protocol for the construction of C–X/C–C bonds via catalytic aminium radical-cation salt (Magic Blue)-initiated SN2-type nucleophilic ring-opening transformations racemic nonracemic aziridines with different hetero carbon nucleophiles to afford various amino ethers, thioethers, amines in up 99% yield, perfect enantiospecificity some substrates but reduced ee others (for aziridines), is developed. This salt-initiated, strategy, along cyclization protocols, employed synthesize biologically significant compounds.

Language: Английский

---

Regioselective Brønsted Acid Catalyzed Ring Opening of Aziridines by Phenols and Thiophenols; A Gateway to Access Functionalized Indolines, Indoles, Benzothiazines, Dihydrobenzo-thiazines, Benzo-oxazines and Benzochromenes

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(27), P. 5653 - 5664

Published: Jan. 1, 2024

A TfOH-catalyzed regioselective ring opening of aziridines by phenols and thiophenols have been reported. Further synthetic transformations lead to access a range useful heterocycles.

Language: Английский

---

Photocatalytic Synthesis of Substituted 2-Aryl Morpholines via Diastereoselective Annulation

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: April 16, 2025

Morpholines are prevalent in medicinal chemistry due to their favorable pharmacokinetic properties and widespread presence FDA-approved drugs. Existing methods for morpholine synthesis often require prefunctionalized or protected reagents, limiting versatility efficiency. Here, we present a photocatalytic, diastereoselective annulation strategy the of morpholines directly from readily available starting materials. This method employs visible-light-activated photocatalyst, Lewis acid, Brønsted acid achieve high yields stereoselectivity. It also provides access diverse substitution patterns, including challenging tri- tetra-substituted morpholines. Mechanistic studies reveal that reaction proceeds through formation radical cation intermediate, with triflic playing critical roles protonating substrate, preserving preventing product oxidation. Beyond morpholines, this is extended piperidines, pyrrolidines, other privileged nitrogen heterocycles. Our findings provide modular approach constructing complex, medicinally valuable scaffolds, advancing both synthetic chemistry.

Language: Английский

---

Rapid Synthesis of 3-Methyleneisoindolin-1-ones via Metal-Free Tandem Reactions of Ester-Functionalized Aziridines

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(7), P. 5153 - 5158

Published: March 14, 2024

We have disclosed a novel metal-free tandem cyclization reaction for the synthesis of 3-methyleneisoindolin-1-ones starting from ester-functionalized aziridines. This strategy can be effectively promoted by DBU and carboxylic acids. Mechanistically, it involves sequential ring opening aziridines with acids, lactamization, elimination

Language: Английский

---

Integrating 3,4-Dihydro-2H-1,4-oxazine into Peptides as a Modification: Silver Triflate-Catalyzed Cyclization of N-Propargyl N-Sulfonyl Amino Alcohols for SPPS Applications

Organic Letters, Journal Year: 2024, Volume and Issue: 26(36), P. 7584 - 7589

Published: Sept. 3, 2024

We present a methodology yielding 3,4-dihydro-2

---

Metal-free anomalous [5+1] cycloaddition reactions of donor–acceptor aziridines for the synthesis of 2H-1,4-oxazines

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(55), P. 8572 - 8575

Published: Jan. 1, 2023

A new type of metal-free [5+1] cycloaddition reaction donor-acceptor aziridines with 2-(2-isocyanoethyl)indoles is reported herein. This method exhibits broad substrate scope and atom-economy. series 2H-1,4-oxazines containing an indole heterocycle skeleton were obtained in up to 92% yield under mild conditions. Control experiments revealed that free N-H crucial for the above transformations. The theoretical calculation studies provided guidance on in-depth insight into mechanism hydrogen-bond between carbonyl group was identified lower energy barrier transition states.

Language: Английский

---

Magic Blue-Initiated S_N2-Type Ring Opening of Activated Aziridines: Friedel–Crafts-Type Alkylation of Electron-Rich Arenes/Heteroarenes

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(16), P. 11429 - 11445

Published: Aug. 1, 2024

A transition metal-free, atom-economical, and highly stereospecific synthetic approach to Friedel–Crafts-type alkylation of arenes/heteroarenes has been developed. The protocol involves the catalytic aminium radical-cation salt (Magic Blue)-initiated SN2-type nucleophilic ring opening activated aziridines with give corresponding 2,2-diarylethylamines up 99% yield 85% ee (for nonracemic aziridines) in a very short reaction time. Moreover, on 1,3-dimethylindole benzofuran, undergo domino-ring-opening cyclization (DROC) various biologically significant heterocyclic scaffolds moderate good yields.

Language: Английский

---

A Synthetic Route to Tetrahydro-1H-azepino[4,3,2-cd]indoles via Ring-Opening Cyclization of Activated Azetidines with 4-Bromoindole: Toward a Vasopressin V2 Receptor Antagonist

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(16), P. 11576 - 11587

Published: Aug. 5, 2024

A simple one-pot, two-step strategy for the synthesis of tetrahydro-1

Language: Английский

---

Three-membered ring systems

Progress in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 41 - 58

Published: Jan. 1, 2024

Language: Английский

---