Progress in heterocyclic chemistry, Год журнала: 2023, Номер unknown, С. 427 - 469
Опубликована: Янв. 1, 2023
Язык: Английский
Organic Letters, Год журнала: 2024, Номер 26(1), С. 62 - 67
Опубликована: Янв. 3, 2024
We have found a chameleonic reactivity of imidoyl sulfoxonium ylides. On the one hand, ylides react with electron-deficient reagents, such as alkynyl esters, to lead formation 1,2-dihydro-pyridines. The methyl group attached sulfur atom acts methylene donor. other pyridinium 1,4-zwitterionic thiolates, which leads functionalized pyrroles. Both transformations feature mild reaction conditions and good functional tolerance.
Язык: Английский
Процитировано
9
The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(14), С. 10180 - 10196
Опубликована: Июль 4, 2024
Presented herein are novel syntheses of CF
Язык: Английский
Процитировано
9
The Journal of Organic Chemistry, Год журнала: 2025, Номер 90(4), С. 1663 - 1670
Опубликована: Янв. 21, 2025
1H-Isochromene scaffolds are ubiquitous in natural products and significant bioactive molecules. Although several methods for these molecular syntheses have been developed, reports on the efficient construction of iminated isochromenes still rather limited. Herein, we report a new Cu(II)-catalyzed annulation sulfonylimination cascade α-carbonyl-γ-alkynyl sulfoxonium ylides with sulfamides, enabling direct C-C σ-bond elimination to furnish (Z)-1H-isochromenes 51-97% yields. During reaction process, ylide unit as traceless eliminative group is key successful sulfonylimination, which enables N-H insertion subsequent acetic acid-mediated elimination.
Язык: Английский
Процитировано
1
The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(3), С. 1898 - 1906
Опубликована: Янв. 17, 2023
A new efficient and stereoselective synthesis of 12-tetrazolyl substituted (E)-5H-quinazolino[3,2-a]quinazolines via sequential Ugi-azide/Staudinger/aza-Wittig/addition/Ag(I)-catalyzed cyclization was developed. The four-component reactions 2-azidobenzaldehyde, 2-(alkynyl)benzenamine, isocyanide, trimethylsilyl azide gave Ugi-azide intermediates, which were subsequently treated with triphenylphosphine isocyanate to produce in the presence Ag(I) catalyst K2CO3.
Язык: Английский
Процитировано
14
Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(11), С. 2557 - 2564
Опубликована: Март 22, 2024
Abstract An iodine/DMSO‐promoted approach has been developed for the synthesis of indoloquinolines via a sequential sp 3 C−H oxidation/intramolecular cyclization using 2‐(1 H ‐indol‐2‐yl)anilines and aryl methyl ketones. A wide range ketones, including drugs complex bioactive molecule‐derived substrates were compatible in present reaction with yields 30–96%. This protocol proceeds through oxidation ketones to phenylglyoxals, subsequent imine formation, furnish indoloquinolines. Further, is applicable gram‐scale operationally simple.
Язык: Английский
Процитировано
5
The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(17), С. 12204 - 12227
Опубликована: Авг. 9, 2024
Herein, a straightforward facile synthesis of indolo[2,3-c]quinoline analogues was reported from 2-arylamino(phenylsulfonyl)methylindoles involving PIDA/BF3·OEt2-mediated intramolecular dehydrogenative coupling (IDC) as key step. Even though isomeric 3-arylamino(phenylsulfonyl)methylindoles, upon interaction with PIDA/BF3·OEt2, led to complications, the indolo[3,2-c]quinoline framework could be easily achieved N-(2-iodoaryl)-N-indolylmethylbenzenesulfonamide by employing Pd(0)-mediated cyclization reaction. Under identical conditions, indolo[2,3-c]quinolines also accomplished respective N-(2-iodoaryl)-N-indolylmethylbenzenesulfonamides. The SRB assay fluorine-bound indoloquinolines displayed nanomolar-level cytotoxicity against nonsmall lung cancer cell line, NCI-H460.
Язык: Английский
Процитировано
2
The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(13), С. 8781 - 8790
Опубликована: Июнь 5, 2023
Reactions involving C(sp3)-H bonds of azaarenes have been widely studied in recent years as they allow direct functionalization these N-heterocycles without the use harsh reaction conditions. In this work, we describe 4-methylquinazolines and 1-benzylisoquinolines, employing α-substituted β-nitrostyrenes catalyzed by inexpensive copper acetate. Under optimized condition, 21 pyrrolo[1,2-c]quinazolines, well an imidazo[1,2-c]quinazoline 4 pyrrolo[2,1-a]isoquinolines, were obtained moderate to good yields. Furthermore, biological activity pyrrolo[1,2-c]quinazolines was evaluated against Plasmodium falciparum, promising results obtained.
Язык: Английский
Процитировано
4
Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(31), С. 6342 - 6351
Опубликована: Янв. 1, 2024
A facile strategy for the synthesis of valuable indolines has been developed, involving a palladium(II)/Brønsted acid co-catalyzed annulation readily available (2-aminophenyl)methanols and sulfoxonium ylides. This protocol allows direct utilization OH group as leaving group, tolerates alkyl aryl groups on N atom aniline moiety, operates under mild reaction conditions, exhibits good efficiency.
Язык: Английский
Процитировано
1
The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown
Опубликована: Сен. 27, 2024
A metal-free approach for synthesizing hybrid quinoxaline derivatives from sulfoxonium ylide and a 1,5-bis-nucleophilic N-heterocycle mediated by elemental sulfur is presented to illuminate the [5+1] cascade cyclization sequence. Large-scale synthesis postsynthetic functionalizations annulative π-extension intramolecular aza-annulation reactions reveal potential utility actualize fabricated approach.
Язык: Английский
Процитировано
1
Tetrahedron Letters, Год журнала: 2024, Номер unknown, С. 155438 - 155438
Опубликована: Дек. 1, 2024
Язык: Английский
Процитировано
1