Utility of 4‐Amino‐2,1,3‐benzothiadiazole Directing Group in the Pd(II)‐catalyzed Arylation of γ‐C−H Bonds of Carboxamides and β‐C‐H Bonds of Amino Acid Carboxamides DOI
Narendra Bisht, Srinivasarao Arulananda Babu, Radha Tomar

и другие.

Asian Journal of Organic Chemistry, Год журнала: 2022, Номер 11(12)

Опубликована: Ноя. 17, 2022

Abstract Expanding the availability, scope, and limitations of directing groups (DGs) for executing site‐selective C−H activation functionalization substrate scope development are valuable efforts. This paper reports extension utility 4‐amino‐2,1,3‐benzothiadiazole (ABTD) group in Pd(II)‐catalyzed arylation remote sp 2 /sp 3 γ‐C−H bonds aromatic carboxamides β ‐C−H amino acid carboxamides. The performance ABTD DG was compared with other known DGs. For example, we have observed that mono methyl alanine carboxamide possessing iodopyridine yielded pyridylalanine derivative. Conversely, same reaction using 8‐AQ did not yield expected Furthermore, 2,1,3‐benzothiadiazole moiety‐containing compounds an important class molecules materials chemistry medicinally relevant molecules. While this work reveals as including derivatives. On hand, indirectly process ABTD‐aided reactions has enabled to accomplish synthesis a library moiety containing new

Язык: Английский

Construction of β‐Phenylalanine Derivatives through Pd‐Catalyzed, C(sp2)−H (ortho) Functionalization DOI

Urja Narang,

Prabhakar Singh, Srinivasarao Arulananda Babu

и другие.

European Journal of Organic Chemistry, Год журнала: 2023, Номер 26(29)

Опубликована: Июнь 13, 2023

Abstract This paper describes the Pd(II)‐catalyzed, picolinamide‐directing‐group‐aided C(sp 2 )−H ( ortho ) functionalization of racemic and enantiopure β ‐phenylalanines 3‐amino‐3‐phenylpropanols (1,3‐amino alcohols). The functionalizations including arylation, bromination, iodination, alkoxylation were attempted. arylation reactions gave biaryl or terphenyl‐type ‐phenylalanine scaffolds, halogenation methoxylation C−H halogenated methoxylated ‐phenylalanines. Additionally, an ‐methyl substituted containing both remote 3 bonds was investigated. ‐Phenylalanine is arylated ‐amino acid motif present in various natural products, bioactive molecules, ‐peptides it a precursor to medicinally active compounds. Accordingly, this work contributes expansion library unnatural acid) derivatives through site‐selective functionalization.

Язык: Английский

Процитировано

7

The recent advances in cobalt-catalyzed C(sp3)–H functionalization reactions DOI
Bhargav Desai,

Ajay Uppuluru,

Ashutosh Dey

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 21(4), С. 673 - 699

Опубликована: Дек. 22, 2022

Over the past decades, reactions involving C-H functionalization have become a hot theme in organic transformations because they lot of potential for streamlined synthesis complex molecules. C(sp3)-H bonds are present most species. Since molecules massive significance various aspects life, exploitation and hold enormous importance. In recent years, first-row transition metal-catalyzed direct selective has emerged as simple environmentally friendly synthetic method due to its low cost, unique reactivity profiles easy availability. Therefore, research advancements being made conceive catalytic systems that foster under benign reaction conditions. Cobalt-based catalysts offer mild convenient conditions at reasonable expense compared conventional 2nd 3rd-row metal catalysts. Consequently, probing Co-based is one topics from outlook an chemist. This review primarily focuses on literature 2018 2022 sheds light substrate scope, selectivity, benefits limitations cobalt transformations.

Язык: Английский

Процитировано

11

Pd(ii)-catalyzed selective β-C–H functionalization of azobenzene carboxamides DOI

Rayavarapu Padmavathi,

Srinivasarao Arulananda Babu

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(13), С. 2689 - 2694

Опубликована: Янв. 1, 2023

We report a Pd(II)-catalyzed bidentate directing group 8-aminoquinoline-aided, site-selective β-C-H functionalization protocol for assembling modified azobenzene carboxamides. Considering the importance of azobenzenes in chemical sciences, this paper reports new route enriching library motifs.

Язык: Английский

Процитировано

6

Recent advances in anti-inflammatory active components and action mechanisms of natural medicines DOI
Zhimin Wu, Tao Zhang, Xiaofei Ma

и другие.

Inflammopharmacology, Год журнала: 2023, Номер 31(6), С. 2901 - 2937

Опубликована: Ноя. 10, 2023

Язык: Английский

Процитировано

6

Pd(II)-Catalyzed, Picolinamide-Aided γ-(sp2)-C–H Functionalization of Racemic and Enantiopure α-Methylbenzylamine and Phenylglycinol Scaffolds DOI
Narendra Bisht, Prabhakar Singh, Srinivasarao Arulananda Babu

и другие.

Synthesis, Год журнала: 2022, Номер 54(18), С. 4059 - 4094

Опубликована: Апрель 20, 2022

Abstract In this paper, we report the Pd(II)-catalyzed, picolinamide DG-aided sp2 γ-C–H functionalization and expansion of library enantiopure α-methylbenzylamine phenylglycinol scaffolds. We have shown synthesis a wide range racemic ortho-C–H arylated, alkylated, brominated, iodinated Various R S (chiral) functionalized scaffolds were synthesized with good enantiopurities. Racemic derivatives are important building blocks in organic medicinal chemistry. Accordingly, work contributes to libraries motifs substrate scope development through Pd(II)-catalyzed bidentate directing group picolinamide-aided site-selective C–H activation method.

Язык: Английский

Процитировано

10

The Recent Advances in Iron‐Catalyzed C(sp3)−H Functionalization DOI

Desai Bhavyesh,

Sudha Soliya,

Ramaiah Konakanchi

и другие.

Chemistry - An Asian Journal, Год журнала: 2023, Номер 19(5)

Опубликована: Дек. 27, 2023

Abstract The use of iron as a core metal in catalysis has become research topic interest over the last few decades. reasons are clear. Iron is most abundant transition on Earth's crust and it widely distributed across world. It been extracted processed since dawn civilization. All these features render noncontaminant, biocompatible, nontoxic, inexpensive therefore constitutes perfect candidate to replace noble metals (rhodium, palladium, platinum, iridium, etc.). Moreover, direct C−H functionalization one efficient strategies by which introduce new functional groups into small organic molecules. majority compounds contain C(sp 3 )−H bonds. Given enormous importance molecules so many aspects existence, utilization bioactivity bonds utmost importance. This review sheds light substrate scope, selectivity, benefits, limitations catalysts for bond activations. An overview activation protocols summarized herein up 2022.

Язык: Английский

Процитировано

5

Pd(II)‐Catalyzed, γ‐C(sp2)−H Alkoxylation in α‐Methylbenzylamine, Phenylglycinol, 3‐Amino‐3‐Phenylpropanol Toward Enantiopure Aryl Alkyl Ethers DOI

Yashika Aggarwal,

Rayavarapu Padmavathi,

Prabhakar Singh

и другие.

Asian Journal of Organic Chemistry, Год журнала: 2022, Номер 11(9)

Опубликована: Авг. 8, 2022

Abstract This paper reports the synthesis of enantiopure aryl alkyl ethers via Pd(II)‐catalyzed picolinamide‐aided γ ‐C(sp 2 )−H alkoxylation various α ‐alkylbenzylamine derivatives using alcohols. Enantiopure ‐methylbenzylamines and amino alcohol substrates such as 2‐amino‐2‐phenylethanol (phenylglycinol) 3‐amino‐3‐phenylpropanol were subjected to (etherification) with alcohols PIDA. ‐Alkylbenzylamines phenylglycinols are valuable building blocks in organic medicinal chemistry research areas. Accordingly, this work has enabled assembling ortho ‐alkoxylated ‐methylbenzylamine containing ether functionality. We have shown utility for ‐methylbenzylamine‐based sulfamoylcarbamates carboxamides which structurally related bio‐active compounds known literature. demonstrates substrate scope elaboration C−H functionalization etherification through C−O bond‐forming process functionality ‐alkylbenzylamines.

Язык: Английский

Процитировано

7

Azobenzene-based unnatural amino acid scaffolds via a Pd(ii)-catalyzed C(sp3)–H arylation strategy DOI
Radha Tomar,

Sonam Suwasia,

Angshuman Roy Choudhury

и другие.

Chemical Communications, Год журнала: 2022, Номер 58(93), С. 12967 - 12970

Опубликована: Янв. 1, 2022

Azobenzene-based unnatural amino acid motifs were constructed via the Pd( ii )-catalyzed diastereoselective β-C(sp 3 )–H arylation and Mills azo coupling tactics.

Язык: Английский

Процитировано

7

Pd(ii)-catalyzed coupling of C–H bonds of carboxamides with iodoazobenzenes toward modified azobenzenes DOI

Sonam Suwasia,

Sugumar Venkataramani, Srinivasarao Arulananda Babu

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(8), С. 1793 - 1813

Опубликована: Янв. 1, 2023

In this paper, we report a synthetic protocol for the construction of biaryl motif-based or π-extended azobenzene and alkylated derivatives via Pd(II)-catalyzed bidentate directing group (DG)-aided C-H activation functionalization strategy. past, synthesis azobenzenes was accomplished through traditional cross-coupling reaction involving organometallic reagents aryl halides equivalent coupling partners. We have shown direct bonds aromatic/aliphatic carboxamides (possessing DG) with iodoazobenzenes as partners DG-aided, site-selective method. Azobenzene-containing compounds are versatile class photo-responsive molecules that found applications across branches chemical, biological materials sciences prevalent in medicinally relevant molecules. Accordingly, new functionalized azobenzene-based scaffolds has been an attractive topic research. Although classical methods efficient, they need pre-functionalized starting materials. This Pd(II)-catalyzed, group-aided arylation aromatic aliphatic using iodoazobenzene partner affording is additional route also contribution towards enriching library modified azobenzenes. photoswitching properties representative synthesized

Язык: Английский

Процитировано

4

Pd(II)-Catalyzed Directing-Group-Aided C–H Arylation, Alkylation, Benzylation, and Methoxylation of Carbazole-3-carboxamides toward C2,C3,C4-Functionalized Carbazoles DOI
Srinivasarao Arulananda Babu, Ramandeep Kaur,

Harcharan Singh

и другие.

Synthesis, Год журнала: 2023, Номер 55(21), С. 3535 - 3567

Опубликована: Март 16, 2023

Abstract We report the Pd(II)-catalyzed β-C–H arylation, alkylation, benzylation, and methoxylation of carbazole-3-carboxamide carbazole-2-carboxamide substrates, assisted by bidentate directing groups 8-aminoquinoline or 2-(methylthio)aniline, construction C2,C3,C4-functionalized carbazole motifs. The arylation reaction was attempted using different such as 8-aminoquinoline, 4-amino-2,1,3-benzothiadiazole, 4-methoxyquinolin-8-amine, butan-1-amine. Through optimization reactions, 2-(methylthio)aniline were found to be suitable and, especially, an efficient group in carbazole-3-carboxamide, substrates. An ample number arylated, alkylated, benzylated, methoxylated carbazole-3-carboxamides synthesized. structures representative β-C(2)–H arylated motifs unequivocally confirmed single-crystal X-ray structure analysis. Given wide range applications carbazoles chemistry, materials sciences, medicinal chemistry there have been constant efforts for developing new methods synthesizing functionalized carbazoles. This work contributes expansion library through a directing-group-aided site-selective activation functionalization carbazole-3-carboxamides.

Язык: Английский

Процитировано

4