Recent advances in the synthesis of N-heterocycles from α-amino acids mediated by iodine DOI
Dongsheng Yang, Jia‐Chen Xiang, An‐Xin Wu

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

The synthesis of N-heterocycles has received extensive attention from scientists considering their important role in organic synthesis, pharmaceuticals, and materials chemistry. α-Amino acids (α-AAs), both natural non-natural, are structurally diverse, containing basic amino groups, acidic carboxyl various side-chain R groups a single molecule. Given structural properties wide range sources, they have undoubtedly become suitable synthetic building blocks for synthesis. However, conventional transformations (AAs) focus on the independently. Conversions these two prominent functional generally do not affect alpha positions branched chains. Over past decade, with application iodine (I

Language: Английский

I2/DMSO-mediated substrate selective oxidation of tetrahydro indole2,4-dione towards 4-hydroxy isatins and 5,6-dihydro-1H-indole-2,4-dione derivatives DOI
Goutam Sinha, Sayan Pramanik, Debashis Jana

et al.

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(28), P. 12544 - 12552

Published: Jan. 1, 2024

Synthesis of tetrahydro indole-2,4-diones from readily available β-enaminones and glyoxal subsequent I 2 /DMSO-mediated oxidation/aromatization indole-2,4-dione to produce 4-hydroxyisatin derivatives.

Language: Английский

Citations

0

From an Azaarene to the Spine of Fused Bicyclics: Cycloaddition-Induced Scaffold Hopping of 5-Hydroxypyrazoles DOI
An‐Xin Wu

Research Square (Research Square), Journal Year: 2024, Volume and Issue: unknown

Published: July 9, 2024

Abstract Skeleton editing for heteroarenes, especially pyrazoles, is challenging and remains scarce due to these non-strained aromatics feature inert reactivities therefore relatively inactive perform a dearomatization/cleavage sequence. Herein, we disclose cycloaddition-induced scaffold hopping of 5-hydroxypyrazoles access pyrazolopyridopyridazin-6-one skeleton in single-operation protocol. By converting five-membered azaarene into five-unit spine 6/6 fused-bicyclics, this work has unlocked new ring-opening reactivity pyrrole core that involves formal C = N bond cleavage while retaining the highly reactive N-N resulting product. A [4 + 2] cycloaddition temporary dearomatized 5-hydroxypyrrole with anin situgenerated aza-1,3-diene follow-up oxidative C-N accounted domino pathway. library pyrazolopyridopyridazin-6-one, which are medicinally relevant nitrogen-atom-rich tricyclics, was obtained efficiently from readily available materials.

Language: Английский

Citations

0

One‐Pot Synthesis of 3‐Hydroxy‐1H‐Pyrrolo[3,4‐b]quinolin‐1‐one via Enaminamides DOI

Xi Shen,

Zhi‐Cheng Yu,

You Zhou

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(21), P. 4399 - 4403

Published: July 16, 2024

Abstract A multicomponent cascade cyclization reaction using aryl methyl ketones, amines, and enaminamide reagents to construct 3‐hydroxy‐1 H ‐pyrrolo[3,4‐ b ]quinolin‐1‐one skeleton with good substrate compatibility (50 examples) has been reported. The one‐pot, metal‐free process formed two C−C bonds, C−N a tetrasubstituted carbon stereocenter containing hydroxyl group. enabled modified transformation of drug molecules derivatization products.

Language: Английский

Citations

0

Divergent Synthesis of Pyrrolidone Fused Pyrimido[1,2-b]indazole through Selective Trapping of Enone Intermediate by 1H-indazol-3-amine DOI

Xi Shen,

Zhi‐Cheng Yu,

You Zhou

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(72), P. 9781 - 9784

Published: Jan. 1, 2024

An oxidant-controlled divergent synthesis of a pyrrolidone fused pyrimido[1,2- b ]indazole skeleton was developed through selective cyclization an in situ generated enone intermediate and 1 H -indazol-3-amine.

Language: Английский

Citations

0

I2-catalyzed tandem sp3 C–H oxidation and annulation of aryl methyl ketones with amidoximes for the synthesis of 5-aroyl-1,2,4-oxadiazoles DOI

Shiva Kumar Punna,

Mariyaraj Arockiaraj,

Venkatachalam Rajeshkumar

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(36), P. 7478 - 7484

Published: Jan. 1, 2024

A metal-free, iodine-catalyzed protocol for the synthesis of biologically significant 5-aroyl 1,2,4-oxadiazole scaffolds has been developed using aryl methyl ketones and amidoximes.

Language: Английский

Citations

0

Iodine‐Mediated Oxidative C=C Double‐Bond Formation toward Fused Quinolinones and Quinolinium Salts DOI

Manman Wang,

Yanmin He,

Junbiao Chang

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 29, 2024

Abstract An iodine‐mediated C=C double bond‐forming reaction has been established to access various fused quinolinone derivatives under transition metal‐free conditions. The present is also applicable the synthesis of quinolinium frameworks from corresponding precursors and can be conducted on a gram scale.

Language: Английский

Citations

0

Electrochemical Synthesis of Quinazolines: N–H/C(sp3)–H Coupling of o-Carbonyl Anilines with Amino Acids and Amines DOI
Jiwei Wu,

Lingxiang Yu,

Kaixuan Li

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 11, 2024

A mild and efficient electrochemical protocol for the synthesis of quinazolines through N-H/C(sp

Language: Английский

Citations

0

Recent advances in the synthesis of N-heterocycles from α-amino acids mediated by iodine DOI
Dongsheng Yang, Jia‐Chen Xiang, An‐Xin Wu

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

The synthesis of N-heterocycles has received extensive attention from scientists considering their important role in organic synthesis, pharmaceuticals, and materials chemistry. α-Amino acids (α-AAs), both natural non-natural, are structurally diverse, containing basic amino groups, acidic carboxyl various side-chain R groups a single molecule. Given structural properties wide range sources, they have undoubtedly become suitable synthetic building blocks for synthesis. However, conventional transformations (AAs) focus on the independently. Conversions these two prominent functional generally do not affect alpha positions branched chains. Over past decade, with application iodine (I

Language: Английский

Citations

0