Pd-Catalyzed Remote δ-C(sp2)–H Functionalization in Phenylalaninol: Expanding the Library of Phenylalaninols DOI
Srinivasarao Arulananda Babu, Prabhakar Singh

Synthesis, Год журнала: 2023, Номер 55(24), С. 4113 - 4144

Опубликована: Авг. 2, 2023

Abstract We report the Pd(II)-catalyzed, picolinamide-directed δ-C(sp2)–H (ortho) functionalization of phenylalaninol scaffolds. Assembling δ-C–H arylated, alkylated, benzylated, alkenylated, brominated, and iodinated scaffolds was accomplished. The arylation reaction occurred under neat conditions. Hydrolysis picolinamide moiety synthetic utility arylated substrates were explored. have also shown preparation some modified Matijin–Su (aurantiamide) derivatives using bis compounds obtained from (Matijin–Su is an anti-HBV agent possessing unit). Considering importance phenylalaninols, this work contributes to expanding library demonstrates substrate scope development in remote reactions.

Язык: Английский

Pd‐Catalyzed Arylation and Benzylation of Tyrosine at the δ−C(sp2)−H and C(2) Positions: Expanding the Library of Unnatural Tyrosines DOI
Prabhakar Singh, Srinivasarao Arulananda Babu

European Journal of Organic Chemistry, Год журнала: 2023, Номер 26(31)

Опубликована: Июнь 20, 2023

Abstract This paper describes Pd(II)‐catalyzed picolinamide‐directed intermolecular arylation and benzylation of remote δ −C(sp 2 )−H bond (C(2) position) the aryl ring in tyrosine derivatives expansion library unnatural tyrosine. Various racemic enantiopure bis C(2) ( ortho C−H) arylated benzylated were assembled good yields. Removal picolinoyl moiety after C(2)−H assembling tyrosine‐based peptides using tyrosines shown. Tyrosine biaryl amino acids are vital scaffolds medicinal chemistry. Correspondingly, this work is a contribution towards with biaryl‐ or terphenyl diarylmethane‐based scaffolds.

Язык: Английский

Процитировано

9
Picolinamide-assisted ortho-C–H functionalization of pyrenylglycine derivatives using aryl iodides DOI
Arup Dalal,

Subhankar Bodak,

Srinivasarao Arulananda Babu

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(6), С. 1279 - 1298

Опубликована: Янв. 1, 2024

Chemical transformations involving pyrenylglycine are seldom known. This paper reports the synthesis of C(2)-arylated (an unnatural amino acid) motifs via a Pd( ii )-catalyzed C–H functionalization and arylation in non-K-region pyrene.

Язык: Английский

Процитировано

3
Construction of Biaryl Sulfonamides via Pd(II)-Catalyzed Cross-Coupling of C(sp2)-H Bonds with Iodobenzenesulfonamides DOI Creative Commons

Debabrata Bhattacharya,

S. C. Pal,

Indranil Banerjee

и другие.

ACS Omega, Год журнала: 2025, Номер unknown

Опубликована: Апрель 21, 2025

This study describes the utility of Pd(II)-catalyzed C-H arylation benzamides for constructing biaryl sulfonamides. Sulfonamides are known their promising applications in pharmaceuticals and agrochemicals. A literature review revealed that sulfonamides were generally constructed via traditional cross-coupling reactions. We report a progressive method obtaining bidentate directing group (8-aminoquinoline or picolinamide)-assisted sp2 bonds aromatic carboxamides with iodobenzenesulfonamides. After reactions, we attempted removal 8-aminoquinoline from synthesized scaffolds possessing carboxamide sulfonamide moieties using triflic acid. In some cases, observed occurrence decarboxylation Friedel-Crafts acylation, affording interesting moiety. The current work contributes toward developing alternative ways assembling various

Язык: Английский

Процитировано

0
Recent Advances in C–H Functionalization of Pyrenes DOI Creative Commons
Srinivasarao Arulananda Babu, Arup Dalal,

Subhankar Bodak

и другие.

Chemistry, Год журнала: 2023, Номер 5(4), С. 2713 - 2755

Опубликована: Дек. 11, 2023

In recent years, transition metal-catalyzed C–H activation and site-selective functionalization have been considered to be valuable synthetic tactics functionalize organic compounds containing multiple bonds. Pyrene is one of the privileged notorious polycyclic aromatic hydrocarbons. its derivatives found applications in various branches chemical sciences, including chemistry, biology, supramolecular material sciences. Given importance pyrene derivatives, several classical methods, method, developed for synthesizing modified scaffolds. This review attempts cover developments area pertaining modification motif through process bonds present motif, leading functionalized pyrenes.

Язык: Английский

Процитировано

4
Fluorene and Fluorenone Unnatural Amino Acid Motifs via Diastereoselective Pd(II)‐Catalyzed sp3C−H Functionalization DOI

Shefali Banga,

Srinivasarao Arulananda Babu

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(23)

Опубликована: Апрель 17, 2024

Abstract This paper reports the construction of racemic and enantiopure (D‐ L‐) fluorene fluorenone‐based novel unnatural amino acid derivatives. The Pd(II)‐catalyzed bidentate directing group‐aided arylation prochiral β ‐C(sp 3 )‐H bonds in racemic, carboxamides acids with iodofluorenes was reported. examples fluorenone motifs containing comprising norvaline, leucine, phenylalanine, norleucine, 2‐aminooctanoic derivatives having anti ‐stereochemistry (with good enantiopurity) accomplished. bis fluorenyl alanine scaffolds motif‐containing non‐ α ‐amino (aminoalkanoic acid) also Examples removal group (8‐aminoquinoline) phthalimide‐protecting present fluorenyl‐based have been shown. Accordingly, motif‐based esters free group‐containing were synthesized. stereochemistry major ( ) diastereomers obtained via ascertained from X‐ray structure a representative compound. Fluorene‐ are vital skeletons materials medicinal chemistry research. this work is contribution towards enriching library scaffolds.

Язык: Английский

Процитировано

1
Synthesis of biaryl-based carbazoles via C-H functionalization and exploration of their anticancer activities DOI
Ramandeep Kaur, Haritha Dilip, Sivapriya Kirubakaran

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(45), С. 8916 - 8944

Опубликована: Янв. 1, 2024

We described the application of C–H functionalization for constructing carbazole-based biaryls and their anticancer activities in cancer cell lines, e.g. , HeLa, HCT116, MDA-MB-231 MDA-MB-468 human embryonic kidney line HEK293T.

Язык: Английский

Процитировано

1
Pd-Catalyzed Remote δ-C(sp2)–H Functionalization in Phenylalaninol: Expanding the Library of Phenylalaninols DOI
Srinivasarao Arulananda Babu, Prabhakar Singh

Synthesis, Год журнала: 2023, Номер 55(24), С. 4113 - 4144

Опубликована: Авг. 2, 2023

Abstract We report the Pd(II)-catalyzed, picolinamide-directed δ-C(sp2)–H (ortho) functionalization of phenylalaninol scaffolds. Assembling δ-C–H arylated, alkylated, benzylated, alkenylated, brominated, and iodinated scaffolds was accomplished. The arylation reaction occurred under neat conditions. Hydrolysis picolinamide moiety synthetic utility arylated substrates were explored. have also shown preparation some modified Matijin–Su (aurantiamide) derivatives using bis compounds obtained from (Matijin–Su is an anti-HBV agent possessing unit). Considering importance phenylalaninols, this work contributes to expanding library demonstrates substrate scope development in remote reactions.

Язык: Английский

Процитировано

0