Brønsted acid catalyzed remote C6 functionalization of 2,3-disubstituted indoles with β,γ-unsaturated α-ketoester DOI Creative Commons

You‐Ya Zhang,

Lin Li, Xiang‐Zhi Zhang

и другие.

Frontiers in Chemistry, Год журнала: 2022, Номер 10

Опубликована: Сен. 13, 2022

A metal-free catalytic approach for the remote C6-functionalization of 2,3-disubstituted indoles has been developed. In presence amounts Brønsted acid, β,γ-unsaturated α-ketoesters react with at C6 position selectively. Under mild reaction conditions, a range C6-functionalized were prepared good yields and excellent regioselectivity. This methodology provides concise efficient route synthesis indole derivatives.

Язык: Английский

Structure‐Guided Mutagenesis Reveals the Catalytic Residue that Controls the Regiospecificity of C6‐Indole Prenyltransferases DOI Creative Commons

Ahmed R Aoun,

Nagaraju Mupparapu,

Diem N. Nguyen

и другие.

ChemCatChem, Год журнала: 2023, Номер 15(11)

Опубликована: Май 8, 2023

Abstract Indole is a significant structural moiety and functionalization of the C−H bond in indole‐containing molecules expands their chemical space, modifies properties and/or activities. prenyltransferases (IPTs) catalyze direct regiospecific installation prenyl moieties on indole‐derived compounds. IPTs have shown relaxed substrate flexibility enabling them to be used as tools for indole functionalization. However, mechanism by which certain target specific carbon position not fully understood. Herein, we use structure‐guided site‐directed mutagenesis, vitro enzymatic reactions, kinetics structural‐elucidation analogs verify key catalytic residues that control regiospecificity all characterized C6 IPTs. The presented results also demonstrate substitution PriB_His312 Tyr leads synthesis prenylated at different positions than C6. This work contributes understanding how can access challenging

Язык: Английский

Процитировано

3

A facile synthesis of pyrrolo[2,3‐j]phenanthridines via the cascade reaction of indoleanilines and aldehydes DOI
Wen‐Jun Huang, Zhipeng Chen, Lixia Liu

и другие.

Journal of Heterocyclic Chemistry, Год журнала: 2022, Номер 59(6), С. 1116 - 1122

Опубликована: Янв. 9, 2022

Abstract A facile method for the synthesis of pyrrolo[2,3‐ j ]phenanthridines from indoleanilines and aldehydes in presence Brønsted acid catalyst benzoquinone oxidant has been established. This approach features excellent yields, high efficiency a wide range substrate scope. Mechanism studies exhibited that this reaction was cascade process including acid‐catalyzed condensation with aldehydes, cyclization oxidative aromatization.

Язык: Английский

Процитировано

4

Green One-Pot Syntheses of 2-Sulfoximidoyl-3,6-dibromo Indoles Using N-Br Sulfoximines as Both Brominating and Sulfoximinating Reagents DOI Creative Commons
Xiao Yun Chen,

Yaonan Tang,

Xinran Xiang

и другие.

Molecules, Год журнала: 2023, Номер 28(8), С. 3380 - 3380

Опубликована: Апрель 11, 2023

A green one-pot 2,3,6-trifunctionalization of N-alkyl/aryl indoles was achieved by adding three equivalents N-Br sulfoximine to the indole solution. variety 2-sulfoximidoyl-3,6-dibromo were prepared with 38-94% yields using sulfoximines as both brominating and sulfoximinating reagents. Based on results controlled experiments, we propose that a radical substitution involving 3,6-dibromination 2-sulfoximination occurs in reaction process. This is first time one pot has been achieved.

Язык: Английский

Процитировано

2

Organocatalytic Synthesis of 2,3,4,9‐Tetrahydro‐1H‐carbazole Embedded Styrene Atropisomers DOI
Chandrakanta Parida, Minakshi Devi, Subhas Chandra Pan

и другие.

European Journal of Organic Chemistry, Год журнала: 2023, Номер unknown

Опубликована: Ноя. 16, 2023

Abstract Herein we report the first synthesis of tetrahydrocarbazole embedded styrene atropisomers via reaction between 1‐(aryl‐ethynyl)‐naphthalen‐2‐ol and 2,3,4,9‐tetrahydro‐1 H ‐carbazole. The proceeds through in situ vinylidene ortho ‐quinone methide (VQM) intermediate formation. derivatives were obtained good to high yields with diastereoselectivities a catalytic amount PTSA. A asymmetric version is also reported.

Язык: Английский

Процитировано

2

B(C6F5)3‐Catalyzed 1,4‐Allylation of Azadienes with Allyltrimethylsilanes DOI
Manman Sun, Rong Zhong, Jinshan Li

и другие.

European Journal of Organic Chemistry, Год журнала: 2023, Номер 26(11)

Опубликована: Янв. 13, 2023

Abstract A metal‐free 1,4‐allylation of azadienes with allyltrimethylsilanes catalyzed by B(C 6 F 5 ) 3 has been developed. The high Lewis acidity, good thermal stability, and hydrolytic stability the catalyst make this reaction efficient operationally simple. In contrast to previously reported 1,2‐allylation α,β‐unsaturated imines, is described here for first time. Benzofuran‐, indene‐, dihydronaphthalene‐, chromene‐, benzothiophene‐based allyl arylmethanes have obtained in up 95 % yield.

Язык: Английский

Процитировано

1

C6–H Bond Functionalization of Indoles: A New Gate DOI
Nurullah Saraçoğlu, Yunus Taskesenligil

Synthesis, Год журнала: 2023, Номер 55(21), С. 3417 - 3433

Опубликована: Март 8, 2023

Abstract Indoles are valuable precursors in medicinal, bioorganic, and material chemistry particularly serve as a platform for diversity. However, the scope of C6-functionalization indoles was limited until recently. In this short review, we summarize developments reactions involving transition-metal-catalyzed functionalization Brønsted Lewis acid catalyzed processes. The regioselectivity is controlled by remote-C–H activation hydrogen bond formation. 1 Introduction 2 Transition-Metal-Catalyzed Functionalization 3 Acid-Catalyzed Processes 4 Conclusion

Язык: Английский

Процитировано

1

TfOH-catalyzed direct Michael addition and cascade cyclization reactions of unactivated ketones: A divergent route to functionalized benzofurans and benzofuro[3,2-b]pyridines DOI
Manman Sun,

Jing Gui,

Rong Zhong

и другие.

Tetrahedron, Год журнала: 2023, Номер 137, С. 133394 - 133394

Опубликована: Апрель 1, 2023

Язык: Английский

Процитировано

1

Brønsted acid-catalyzed C6 functionalization of 2,3-disubstituted indoles for construction of cyano-substituted all-carbon quaternary centers DOI
Wen‐Jun Huang, Lixia Liu, Yong‐Gui Zhou

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(17), С. 3691 - 3696

Опубликована: Янв. 1, 2023

The construction of cyano-substituted all-carbon quaternary centers via Brønsted acid-catalyzed direct C6 functionalization 2,3-disubstituted indoles with 2,2-diarylacetonitriles is reported.

Язык: Английский

Процитировано

1

Additive‐Controlled Divergent [4+2] Cycloaddition and 1,4‐Michael Addition Reaction of Benzofuran‐Derived Azadienes with Enamides: Access to Decahydrobenzofuro[3,2‐b]quinolines DOI
Yuqi Tian,

Ruijie Shi,

Limei Gao

и другие.

ChemistrySelect, Год журнала: 2024, Номер 9(26)

Опубликована: Июль 9, 2024

Abstract We describe herein the additive‐controlled divergent [4+2] cycloaddition and 1,4‐Michael addition reaction of benzofuran‐derived azadienes (BDAs) with enamides. An unprecedented BDAs enamide compounds was developed in presence 4 Å MS, providing a variety structurally complex decahydrobenzofuro[3,2‐ b ]quinolines (13 examples) moderate to excellent yields (59–98 % yields) single diastereoisomer obtained. While employing MgSO as desiccant, chemoselectivity switched 1,4‐addition reactions, leading wide range highly functionalized hybrids benzofurans (25 25–94 under mild conditions.

Язык: Английский

Процитировано

0

Efficient Metal-Free Synthesis of Heterotriarylmethanes by 1,4-Addition of Benzofuran Azadienes DOI
Hongli Huang,

Zhongzhong Peng,

Fei Gao

и другие.

Synlett, Год журнала: 2024, Номер unknown

Опубликована: Июль 22, 2024

Abstract A novel and efficient method has been established for synthesizing a variety of heterotriarylmethanes with good yields by employing metal-free self-coupling reaction benzofuran azadienes. The involvement t-BuONa is essential in this process. Remarkably, technique boasts mild conditions exceptional compatibility various functional groups, rendering it versatile invaluable asset the realm organic synthesis.

Язык: Английский

Процитировано

0