Radical Cascade Reaction of Heterocyclic Ketene Aminals with Thiocyanates Promoted by Visible Light: Synthesis of Functionalized Fused 2-Iminothiazolines DOI

Shu Shu Yang,

Tingting Guo, Jianbo Ma

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(18), С. 13678 - 13690

Опубликована: Сен. 6, 2024

Herein, a visible-light-promoted radical cascade cyclization of heterocyclic ketene aminals (HKAs) and thiocyanates was developed to access functionalized fused 2-iminothiazolines. This novel reaction can be realized under only visible-light irradiation without the help external photocatalysts, oxidants, additives. These multicomponent reactions demonstrate excellent selectivity for

Язык: Английский

Catalyst-Free Cascade Annulation of Enaminones and Aryl Diazonium Tetrafluoroboronates for Cinnoline Synthesis and the Anti-Inflammatory Activity Study DOI

Shanghui Tian,

Yunyun Liu, Changfeng Wan

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(4), С. 2433 - 2442

Опубликована: Фев. 8, 2023

A simple and concise method for the synthesis of cinnolines has been developed by reactions readily available enaminones aryl diazonium tetrafluoroboronates. The run efficiently to provide with broad diversity in substructure heating dimethyl sulfoxide without using any catalyst or additive. In addition, primary investigation anti-inflammatory activity these products leads observation p-chlorobenzoyl (3f) p-nitrobenzoyl (3j) as attractive compounds vitro.

Язык: Английский

Процитировано

13

Organophotocatalyzed Mono- and Bis-Alkyl/Difluoroalkylative Thio/Selenocyanation of Alkenes DOI

Koustav Pal,

Palasetty Chandu, Debabrata Das

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(24), С. 17527 - 17537

Опубликована: Ноя. 21, 2023

Organophotocatalyzed three-component 1,2-difluoroacetyl/alkyl/perfluoroalkylative thio/selenocyanation of styrene derivatives under stoichiometric, transition metal-, oxidant-, and additive-free, mild redox-neutral conditions is reported. Organophotocatalyst 4CzIPN operates the overall radical-polar-crossover mechanistic cycle via initial oxidative luminescence quenching, key intermediates were experimentally detected. Selective mono-alkylative thiocyanation alkenes using dibromoalkanes also demonstrated. This one-pot synthetic methodology suitable for primary, secondary, tertiary alkyl halides extended double alkylative with excellent yields.

Язык: Английский

Процитировано

9

Iodonium(III) Ylide: An Iodoalkylation Reagent with Aryne DOI
Weigang Xu, Pengfei Li,

Yuerong Li

и другие.

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

Опубликована: Фев. 5, 2025

A tandem Hexadehydro-Diels–Alder (HDDA)/[2 + 2] cycloaddition/aryl migration reaction of iodonium ylide with tetrayne is described, in which served as a unique double bond and reacted aryne to form four-membered iodonium(III) cycle, then converted iodoarene after aryl group from iodine adjacent carbon. This strategy allows the efficient construction fully substituted compounds.

Язык: Английский

Процитировано

0

Dess-Martin Periodinane (DMP) in Organic Synthesis-A Septennial Update (2015-till Date) DOI
Ravi Varala, Vittal Seema, Mohammed Mujahid Alam

и другие.

Current Organic Chemistry, Год журнала: 2023, Номер 27(17), С. 1504 - 1530

Опубликована: Сен. 1, 2023

Abstract: Dess-Martin periodinane (DMP) is one of the hypervalent iodines that most frequently utilized as an oxidizing agent in organic chemistry. The authors this septennial review have critically and methodically presented representative applications DMP synthesis from 2015 to present, including oxidations, dehydrogenations, hetero homo-dimerizations, aromatizations, thiocyanations, halogenations, dearylations, ring expansions, cyclizations, heterocyclic formation, other miscellaneous reactions. This discusses range constraints these transformations.

Язык: Английский

Процитировано

7

NBS-Promoted Synthesis of Thiocyanated Aminomaleimides and Site-Selective Intramolecular Cyclization Access to 1,4-Benzothiazepines via S–CN Bond Cleavage DOI
Qi Yang,

Shuntao Huang,

Lu Yin

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(8), С. 5266 - 5276

Опубликована: Апрель 9, 2024

A transition metal-free concise and efficient protocol for the synthesis of thiocyanated aminomaleimides benzo[e][1,4]thiazepine derivatives has been developed. The method involves an initial α-C–H thiocyanation with KSCN TEMPO-mediated tandem S–CN bond cleavage/intramolecular cyclization substitution processes, which enables formation seven-membered S/N-heterocycles. This synthetic strategy provides a reliable biologically interesting by using as sulfur sources well expands application enaminones reactions in heterocycles synthesis.

Язык: Английский

Процитировано

1

TBAB-catalyzed assisted C-C/C-N bond formations: An efficient approach to dihydrobenzo[ b ][1,8]naphthyridin derivatives via metal free Cascade annulation DOI
Jiming Liu, Xinghua Zheng, Wenjun Luo

и другие.

Synthetic Communications, Год журнала: 2024, Номер 54(15), С. 1252 - 1262

Опубликована: Июль 22, 2024

Язык: Английский

Процитировано

1

Selective Preparation of Pyrrolo[2,3‐c]tetrahydroquinolines and Indolo[3,2‐c]tetrahydroquinolines through N‐Arylation/Cycloaddition/Rearrangement Annulation Reactions of Alkynyl‐Tethered Oximes with Diaryliodonium Salts DOI Open Access

Chang‐Rui Nie,

Mingyao Pan,

Rong Deng

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер unknown

Опубликована: Окт. 25, 2024

Abstract We describe a selective preparation of variety functionalized pyrrolo[2,3‐ c ]tetrahydroquinolines and indolo[3,2‐ in 40–82% 40–80% yields from alkynyl‐tethered oximes with diaryliodonium triflates, respectively. The one‐pot reaction underwent N ‐arylation, intramolecular [3+2] cycloaddition, [1.3] or [3,3]‐rearrangement N−O bond total three steps. Experimental studies revealed that EtOAc solvent copper(II)‐catalyst played crucial roles on the formation these two tetrahydroquinoline scaffolds. Moreover, scaffolds could be converted into various building blocks by further transformations.

Язык: Английский

Процитировано

1

Three Component Synthesis of 4‐Aryl‐2‐aminothiazoles under Transition‐Metal Free Conditions DOI

Xi Cheng,

Da‐Bin Qin,

Zhi‐Bing Dong

и другие.

European Journal of Organic Chemistry, Год журнала: 2023, Номер 26(39)

Опубликована: Авг. 25, 2023

Abstract An efficient three‐component synthesis of 4‐aryl‐2‐aminothiazoles was reported. Phenyl‐thioureas reacted with 2‐bromoacetophenones to form through cyclization, and the subsequent C−N bonding benzyl/allyl bromides gave desired disubstituted thiazoles smoothly. The protocol features transition‐metal free, short reaction time, easily available starting materials, good yields broad substrate scope, showing potential synthetic value for a variety biologically or pharmaceutically active compounds.

Язык: Английский

Процитировано

2

Synthesis of functionalized tetrahydrodibenzo[b,g][1,8]naphthyridin-1(2H)-ones through base-promoted annulation of quinoline-derived dipolarophiles and cyclic enaminones DOI

Wenjun Luo,

Xinghua Zheng,

Fanglian Zhang

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(48), С. 9524 - 9529

Опубликована: Янв. 1, 2023

An eco-friendly and metal-free method for the synthesis of tetrahydrodibenzo[b,g][1,8]naphthyridin-1(2H)-ones was established. Quinoline-derived dipolarophiles cyclic enaminones as starting materials undergo a 1,4-Michael addition/SNAr tandem annulation reaction affording target products. This approach features transition conditions, good functional group tolerance operational simplicity.

Язык: Английский

Процитировано

2

1,3-Thiazole Derivatives as a Promising Scaffold in Medicinal Chemistry: A Recent Overview DOI
Pragati Kushwaha, Shashi Pandey

Anti-Inflammatory & Anti-Allergy Agents in Medicinal Chemistry, Год журнала: 2023, Номер 22(3), С. 133 - 163

Опубликована: Сен. 1, 2023

Abstract: The thiazole ring is a unique heterocyclic motif among compounds. This five-member with one nitrogen and sulphur atom displays wide array of pharmacological activities, including anti-inflammatory, antimicrobial, anticancer, antidiabetic, antiviral, etc., by acting on several targets. Its broad range medical applications has inspired us to study this opulent molecule. current review summarizes synthetic approaches for the preparation derivatives in brief discusses promising biological activities scaffold. will be useful drug discovery community facilitate synthesis development novel potent derivatives, which may serve as lead molecules treatment various diseases.

Язык: Английский

Процитировано

2