Highly Diastereoselective One-Pot Synthesis of 4,5-Dihydrofuro[2,3-b]azocin-6-one Derivatives through Cyclization/[4+4] Annulation Reactions

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(11), P. 6704 - 6715

Published: May 8, 2023

A variety of 4,5-dihydrofuro[2,3-b]azocin-6-one derivatives were expediently assembled through Au(I)-catalyzed cyclization and 2-(tert-butyl)-1,1,3,3-tetramethylguanidine (BTMG)-mediated [4+4] annulation reactions enyne-amides ynones. The exhibit high efficiency with excellent regio- diastereoselectivity. broad spectrum substrates was utilized. products an eight-membered ring might be useful in biological chemistry medicinal science. Furthermore, the could facilely converted into various derivatives.

Language: Английский

---

Photoinduced carbene transfer for copper-catalyzed asymmetric [4 + 1] cycloadditions: an entry to chiral indolines bearing quaternary stereocenters

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(14), P. 3498 - 3503

Published: Jan. 1, 2023

A copper-catalyzed asymmetric [4 + 1] cycloaddition of ethynylbenzoxazinones with sulfur ylides formed in situ by photoinduced carbene transfer is reported to afford chiral indolines good efficiency, enantio- and diastereoselectivities.

Language: Английский

---

Recent advances in [4 + 4] annulation of conjugated heterodienes with 1,4-dipolar species for the synthesis of eight-membered heterocycles

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 22(2), P. 252 - 268

Published: Nov. 28, 2023

Eight-membered heterocycles are important but their synthesis is usually challenging. This review summarizes the recent advances in [4 + 4] annulation of conjugated heterodienes with 1,4-dipolar species for assembling eight-membered heterocycles.

Language: Английский

---

Highly Regio- and Diastereoselective Phosphine-Catalyzed [2 + 4] Annulation of Benzofuran-Derived Azadienes with Allyl Carbonates: Access to Spiro[benzofuran-cyclohexanes]

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(18), P. 13030 - 13041

Published: Aug. 30, 2023

A novel highly regio- and diastereoselective phosphine-catalyzed [2 + 4] annulation of benzofuran-derived azadienes (BDAs) with acidic hydrogen-tethered allyl carbonates has been developed ingeniously. range functionalized spiro[benzofuran-cyclohexane] derivatives two consecutive stereocenters were smoothly obtained in moderate to excellent yields under mild reaction conditions from readily available materials. Moreover, this method is a practical scalable strategy that creates the core structural motif fungistatic drug, griseofulvin.

Language: Английский

---

Substrate-directed divergent annulations of sulfur ylides: synthesis of functionalized bispirocyclopentane and bispirocyclopropane derivatives

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(11), P. 2197 - 2202

Published: Jan. 1, 2024

A substrate-directed divergent [2+3]/[2+1] annulation of tetra-substituted oxa-dienes and allylic sulfur ylides has been developed for the synthesis functionalized bispirocyclopentane bispirocyclopropane derivatives.

Language: Английский

---

One-pot synthesis of 4-(imidazol-1-yl)indole derivatives through a sequential dearomatization and Ag-catalyzed cyclization/Cs₂CO₃-mediated addition/aromatization reaction

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(20), P. 4245 - 4256

Published: Jan. 1, 2023

A convenient one-pot assembly of 4-(imidazol-1-yl)indole derivatives from easily accessible o-alkynylanilines and imidazoles has been developed. The sequential dearomatization Ag(I)-catalyzed cyclization/Cs2CO3-mediated conjugate addition/aromatization cascade reactions exhibit high efficiency excellent selectivity. combined use a silver(I) salt cesium carbonate is significant for facilitating this domino transformation. products could be converted to the corresponding might valuable in biological chemistry medicinal science.

Language: Английский

---

Nitrite-catalyzed economic and sustainable bromocyclization of tryptamines/tryptophols to access hexahydropyrrolo[2,3-b]indoles/tetrahydrofuroindolines in batch and flow

Chinese Chemical Letters, Journal Year: 2023, Volume and Issue: 35(7), P. 109280 - 109280

Published: Nov. 9, 2023

Language: Английский

---

Synthesis of Sulfone Methylene-Substituted Indolines by Radical Cascade Cyclization of 2-Alkynylaniline Derivatives

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10678 - 10683

Published: July 16, 2024

A radical cascade cyclization of 2-alkynylaniline derivatives with sulfonyl chlorides was developed to construct C3-sulfone methylene-substituted indolines in yields 21 85% a broad substrate scope under metal- and base-free conditions. This protocol could simultaneously build three new chemical bonds employ solvent-radical relay strategy, providing rapid concise approach toward an indoline framework. Scale-up reactions this method further transformations afford useful were also demonstrated.

Language: Английский

---

Stereoselective Divergent Synthesis of Chiral Pyrazolone Derivatives via Multicomponent Cascade Reactions by Isothiourea Catalysis

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 26, 2024

Isothiourea-catalyzed multicomponent cascade reactions are challenging due to the existence of competitive side between multiple reaction partners and intermediates. Herein, we report a practical efficient protocol for stereoselective divergent synthesis pyrazolone-derived β-amino acid esters β-lactams by isothiourea catalysis. Two distinct pathways identified, which controlled esterification or lactamization zwitterionic intermediate. The strategy is attractive because convenient one-step procedure, mild conditions, high stereoselectivity, good functional-group tolerance.

Language: Английский

---

Selective N–N or N–S bond cleavage of 1-trifluoromethyl benzotriazoles enables divergent synthesis of 1,2,4-benzotriazines and benzotriazoles

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(20), P. 5138 - 5143

Published: Jan. 1, 2023

A variety of 1,2,4-benzotriazines and benzotriazoles are conveniently divergently synthesized via selective N–N or N–S bond cleavage 1-trifluoromethyl under different basic conditions.

Language: Английский

---