Authorea (Authorea), Год журнала: 2024, Номер unknown
Опубликована: Янв. 30, 2024
The development of efficient and sustainable methods to obtain spirocyclic compounds is significance as these structures are widely found in pharmaceuticals agrochemicals. Herein, we disclose an electrochemical dearomative spirocyclization N-acyl sulfonamides a continuous-flow cell. reaction simple without external catalysts or supporting electrolytes, in-cluding decagram-scale synthesis.
Язык: Английский
The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(19), С. 13610 - 13621
Опубликована: Сен. 11, 2023
An electrophilic spirocyclization of N-benzylacrylamides with N-halosuccinimides (NXS) as the halogenating reagents has been developed. This reaction is carried out at room temperature under simple conditions without relying on metal reagents, photochemistry, or electrochemistry, providing a fast and efficient route to synthesize wide variety 4-halomethyl-2-azaspiro[4.5]decanes satisfactory yields. The approach further highlighted through gram-scale synthesis diverse transformations spiro products.
Язык: Английский
Процитировано
55
Chemical Science, Год журнала: 2024, Номер 15(8), С. 2827 - 2832
Опубликована: Янв. 1, 2024
Efficient control over several possible reaction pathways of free radicals is the chemical basis their highly selective transformations. Among various competing pathways, sulfonimidyl generated from electrolysis 2-alkynylbenzenesulfonamides undergo cascade migratory or
Язык: Английский
Процитировано
7
Tetrahedron Chem, Год журнала: 2024, Номер 9, С. 100055 - 100055
Опубликована: Янв. 14, 2024
This review concentrates on our research into the discovery of novel ynone-based dearomative spirocyclisation processes, whilst placing new chemistry context existing knowledge. The genesis programme, development efficient synthetic routes to prepare natural products spirobacillene A (1) and B (2), utilised indole ynones. stimulated a much wider study explore reactivity ynones in processes more generally. Routes generate wide range spirocycles were subsequently developed, with reactions tethered indoles, benzofurans, benzisoxazoles, pyrroles, pyridines, isoquinolines, pyrazines, cyclic ketimines, anisoles all discussed herein, these initiated by catalytic Ag(I), Cu(II), Pd(0), photolysis many other reagents. Asymmetric variants some are also discussed, as is further elaboration spirocyclic give carbazoles, quinolones, polycycles useful building blocks. Finally, applications methodology product synthesis (e.g. A, lasubine II indolizidine 209D) described.
Язык: Английский
Процитировано
7
Organic Letters, Год журнала: 2024, Номер 26(23), С. 4904 - 4909
Опубликована: Июнь 5, 2024
Herein, we reveal an unprecedented domino annulation of
Язык: Английский
Процитировано
7
Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(31), С. 6379 - 6388
Опубликована: Янв. 1, 2023
Dearomative ipso -annulation of unactivated biaryl ynones using AgSCN/AgSCF 3 as the radical source in presence CAN DMSO is disclosed.
Язык: Английский
Процитировано
16
Organic Letters, Год журнала: 2023, Номер 25(32), С. 6001 - 6005
Опубликована: Авг. 7, 2023
An electrochemical facilitated three-component trifluoromethylation/spirocyclization reaction of N-(arylsulfonyl)acrylamides, CF3SO2Na, and H2O has been developed. Without the requirement chemical oxidants, a number unexplored trifluoromethylated 4-azaspiro[4.5]decanes were obtained in satisfactory yields under mild conditions. This work provides new synthetic strategy for fluorine-containing spirocyclic compounds shows perspective reactivity study N-(arylsulfonyl)acrylamides.
Язык: Английский
Процитировано
11
Organic & Biomolecular Chemistry, Год журнала: 2025, Номер unknown
Опубликована: Янв. 1, 2025
The reaction of N -propiolyl-benzimidazole with aliphatic carboxylic acids in the presence ammonium persulfate leading to pyrrolo-benzimidazolones is presented.
Язык: Английский
Процитировано
0
Organic Letters, Год журнала: 2025, Номер unknown
Опубликована: Март 6, 2025
An electro-oxidative formal (3 + 3) annulation of 1,3,5-triazinanes with enamines toward multisubstituted 1,2-dihydropyrimidines is reported. This metal-free mild protocol offers wide functional group tolerance, and heterocycles an unexplored molecular scaffold were constructed in excellent yields. Mechanistically, the electro-oxidation triazinane nucleophilic reactivity enamine result a concomitant annulation-fragmentation process, leading to six-membered heterocyclic product.
Язык: Английский
Процитировано
0
The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown
Опубликована: Апрель 9, 2025
An unprecedented approach involving radical-mediated sulfonylation/dearomative ipso-annulation of N-(methyl-2-phenylacetate)propiolamides using arylsulfonyl radical, generated from aryl diazonium salt in the presence DABSO, is developed. This strategy provides uniquely substituted 3-sulfonyl azaspiro[4.5]decatrienones good yields. The developed has also been extended fruitfully to 3-thiocyano aza-spirocycles through domino thiocyanation/dearomative ipso-annulation.
Язык: Английский
Процитировано
0
The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(23), С. 16485 - 16496
Опубликована: Ноя. 9, 2023
Till date, the ipso-cyclization of propiolamides is limited to provide azaspiro[4,5]decatrienones. Herein, we present first example ipso-carbocyclization, leading azaspiro[5,5]-undecatrienones from N-propiolyl-2-arylbenzimidazoles, involving both radical-based and electrophilic reactions. This report establishes an access a wide range chalcogenated (SCN/SCF3/SePh) benzimidazo-fused azaspiro[5,5]undecatrienones in good yields.
Язык: Английский
Процитировано
10