Опубликована: Янв. 1, 2023
A new cascade radical addition/cyclization of unactivated alkenes and phosphine oxides has been developed. wide variety bioactive phosphine-containing quinazolinones were obtained in up to 91.3% yield for 29 examples under transition-metal-free conditions. This protocol represents an environmentally friendly efficient way build excellent yields mild conditions with a broad substrate scope high atomic economy.
Язык: Английский
Advanced Synthesis & Catalysis, Год журнала: 2022, Номер 364(6), С. 1085 - 1090
Опубликована: Фев. 10, 2022
Abstract A radical di‐ and trichloromethylation/cyclization of unactivated alkenes was developed with commercially available dichloromethane chloroform as di‐and trichloromethyl sources under metal‐free conditions. Variously substituted trichloromethylated pyrrolo‐ piperidino‐quinazolinones were obtained in 47–94% yields. Additionally, dibromomethylation/cyclization also achieved standard conditions when CH 2 Br utilized. Moreover, the dichloromethylated product can be transformed into 1′ H ‐spiro[cyclopropane‐1,3′‐pyrrolo[2,1‐ b ]quinazolin]‐9′(2′ )‐one after treating by KOH. magnified image
Язык: Английский
Процитировано
39
Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 20(32), С. 6293 - 6313
Опубликована: Янв. 1, 2022
As one of the most important structural units in pharmaceuticals and medicinal chemistry, quinazolinone its derivatives exhibit a wide range biological pharmacological activities, including anti-inflammatory, antitubercular, antiviral, anticancer etc. In particular, 2,3-fused quinazolinones have attracted much attention because rings fused to 2,3-positions improve their rigidity planarity. Their synthetic strategies made great advances recent years. Therefore, this review focuses on novel for synthesis from 2017 2022, such as difunctionalization alkenes, ring-opening easily available small rings, dehydrogenative cross-coupling reactions, transition-metal catalyzed cyclizations, cycloadditions, other cascade reactions.
Язык: Английский
Процитировано
31
The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(15), С. 10146 - 10157
Опубликована: Июль 13, 2022
A mild and facile photo-induced cascade radical addition/cyclization of unactivated alkenes has been reported, through which a variety biologically valuable phosphine-containing quinazolinones could be obtained in moderate to good yields. The protocol was characterized by conditions, broad substrate scope, high atomic economy.
Язык: Английский
Процитировано
30
Asian Journal of Organic Chemistry, Год журнала: 2023, Номер 12(5)
Опубликована: Апрель 8, 2023
Abstract Ring‐fused polycyclic structures widely exist in a myriad of natural products and pharmaceutical molecules. Consequently, the construction such from readily available substrates becomes an important researching topic organic synthesis. Triggered by addition radicals to (activated or unactivated) double bonds alkenes, subsequent intramolecular addition/cyclization leads compounds. Following this procedure, variety functionalized ring‐fused were formed. Great achievements have been witnessed recently. Those works provided efficient, atom economy, operational simple approaches toward versatile alkene‐based substrates. Here, we summarized recent on formation via radical‐triggered cascade reactions alkenes. Construction with no less than 3 fused rings developed during last decade included Review, corresponding mechanisms also discussed.
Язык: Английский
Процитировано
23
Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(11), С. 2241 - 2251
Опубликована: Янв. 1, 2024
A novel cascade radical addition/cyclization reaction of non-activated olefins and oxamic acids has been proposed.
Язык: Английский
Процитировано
5
ACS Catalysis, Год журнала: 2024, Номер 14(8), С. 6001 - 6008
Опубликована: Апрель 5, 2024
We disclose a catalytic photoredox carbobromination of unactivated alkenes with α-bromocarbonyl compounds under blue-light-emitting diode (LED) light. The reaction proceeds α-bromoesters, α-bromonitriles, and α-bromo-γ-lactones along terminal 1,2-disubstituted internal alkenes. Reactions indenes 1,1-disubstituted generate alkylated Mechanistic studies by product selectivity three-way competitive crossover experiments suggest that the operates radical-addition radical-pairing (RARP) mechanism. turnover is achieved single electron reduction PC•+ Br– (or Br3–), rather than alkyl radical (R•), generated pairing Br• Br2•–) R•, instead combination carbocation (R+).
Язык: Английский
Процитировано
5
European Journal of Organic Chemistry, Год журнала: 2023, Номер unknown
Опубликована: Авг. 31, 2023
Abstract Achieving high molecular complexity can be not trivial, but the exploitation of domino reactions provides an atom‐ and step‐economical method to reach this target. Over past decades, a lot efforts have been put on development photocatalytic cascades employing both metal‐based purely organic catalysts. Despite effectiveness these protocols, catalyst‐ additive‐free light‐induced are gaining momentum thank their efficiency, operational simplicity sustainability. The increasing number papers published field in last years is proof appeal transformations. In Review, we discuss multicomponent mediated by light with focus photocatalyst‐ processes. most recent advances synthesis complex nitrogen‐, oxygen‐, sulphur‐ selenium‐heterocycles together analysed emphasis experimental mechanistic studies.
Язык: Английский
Процитировано
10
Journal of Organometallic Chemistry, Год журнала: 2024, Номер 1008, С. 123066 - 123066
Опубликована: Фев. 18, 2024
Язык: Английский
Процитировано
3
Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 20(48), С. 9722 - 9733
Опубликована: Янв. 1, 2022
A mild and efficient transition metal-free radical difluoroarylmethylation/cyclization of unactivated alkenes toward the synthesis quinazolinone derivatives with easily accessible α,α-difluoroarylacetic acids has been developed.
Язык: Английский
Процитировано
11
Tetrahedron, Год журнала: 2023, Номер 148, С. 133669 - 133669
Опубликована: Окт. 4, 2023
Язык: Английский
Процитировано
6