Lewis Acid‐Catalyzed Tandem Annulation of Propargylic Alcohols with 2‐Allylphenols and Their Anti‐tumor Activities DOI
Xiang Li,

Ning-Yu Guo,

Qing-Hui Liu

и другие.

Asian Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Авг. 19, 2024

Abstract A novel bismuth(III) trifluoro‐methanesulfonate‐catalyzed and environmentally benign synthetic strategy for the construction of a wide range structurally diverse, sophisticated [5,6,5]‐oxygen‐containing tricyclic frameworks with easy‐to handle propargylic alcohols 2‐allylphenols as substrates in presence Bi(OTf) 3 AgOTf is described. This Lewis acid catalyzed [3+2] annulation protocol, which tolerates great deal functional groups, proceeds through sequential Meyer‐Schuster rearrangement, nucleophilic substitution, 5‐ exo ‐trig cyclization, endo proton exchange sequences, affording versatile approach accessing oxygen‐containing skeletons moderate‐to‐excellent yields. In addition, most obtained compounds exhibited anti‐tumor activities against three types human cancer cell lines vitro , including Caco‐2 colon cells, MCF‐7 breast Hepg‐2 liver cells.

Язык: Английский

Stereoselective Synthesis of Functionally Rich Spirooctahydroquinoline Oxindoles via Enynamide Cycloisomerisation/[4+2]‐Addition Sequence DOI
Madavi S. Prasad, Aman Kumar Jha,

Sankar Bharani

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(9), С. 2014 - 2019

Опубликована: Март 18, 2024

Abstract Creating an expedient method for synthesizing biologically significant functionally rich octahydroquinoline is a highly sought‐after yet challenging endeavour. In this report, we document unprecedented approach to the construction of novel spirooctahydroquinoline oxindole architectures. The reaction proceeds through Pd (II) catalyzed cycloisomerisation and quinine [4+2]‐addition sequence afford desired adduct in moderate excellent yield (up 89%) single diastereomer with three contiguous stereocenters including one spirocenter. An overwhelming number libraries were generated (35 examples) reflecting synthetic versatility functional groups/substituents tolerance. Further, transformed into medicinally important fluoro‐decahydroepoxyethanoquinoline spirooxindole scaffold five selectivity (95% >99:1 dr) steps which signifies utility developed methodology.

Язык: Английский

Процитировано

1

TMSCl-Promoted Sulfonylation of Propargylic Alcohols with Sodium Sulfinates for the Construction of (E)-1,3-Disulfonylpropenes and (E)-1-Sulfonylpropenols DOI

Shimin Jiang,

Meng Liang,

Xi Chen

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(21), С. 15694 - 15707

Опубликована: Окт. 12, 2024

A direct and novel transformation of propargylic alcohols with sodium sulfinates for the regio- stereoselective synthesis (

Язык: Английский

Процитировано

1

Lewis Acid‐Catalyzed Tandem Annulation of Propargylic Alcohols with 2‐Allylphenols and Their Anti‐tumor Activities DOI
Xiang Li,

Ning-Yu Guo,

Qing-Hui Liu

и другие.

Asian Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Авг. 19, 2024

Abstract A novel bismuth(III) trifluoro‐methanesulfonate‐catalyzed and environmentally benign synthetic strategy for the construction of a wide range structurally diverse, sophisticated [5,6,5]‐oxygen‐containing tricyclic frameworks with easy‐to handle propargylic alcohols 2‐allylphenols as substrates in presence Bi(OTf) 3 AgOTf is described. This Lewis acid catalyzed [3+2] annulation protocol, which tolerates great deal functional groups, proceeds through sequential Meyer‐Schuster rearrangement, nucleophilic substitution, 5‐ exo ‐trig cyclization, endo proton exchange sequences, affording versatile approach accessing oxygen‐containing skeletons moderate‐to‐excellent yields. In addition, most obtained compounds exhibited anti‐tumor activities against three types human cancer cell lines vitro , including Caco‐2 colon cells, MCF‐7 breast Hepg‐2 liver cells.

Язык: Английский

Процитировано

0