Recent advances in microwave-assisted multicomponent synthesis of spiro heterocycles

RSC Advances, Journal Year: 2024, Volume and Issue: 14(8), P. 5547 - 5565

Published: Jan. 1, 2024

Spiro heterocycle frameworks are a class of organic compounds that possesses unique structural features making them highly sought-after targets in drug discovery due to their diverse biological and pharmacological activities.

Language: Английский

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Recent developments on microwave-assisted organic synthesis of nitrogen- and oxygen-containing preferred heterocyclic scaffolds

RSC Advances, Journal Year: 2023, Volume and Issue: 13(47), P. 32858 - 32892

Published: Jan. 1, 2023

This review highlights recent developments in the microwave-assisted organic synthesis of N- and O-containing heterocycles with specific examples pyrazolopyrimidines-, coumarin-, quinoline-, isatin-based scaffolds their associated biological activities.

Language: Английский

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Decarboxylative 1,3-dipolar cycloadditions of l-proline

RSC Advances, Journal Year: 2024, Volume and Issue: 14(12), P. 8481 - 8501

Published: Jan. 1, 2024

1,3-Dipolar cycloaddition is one of the important chemical reactions between a 1,3-dipole and dipolarophile to construct five-membered heterocyclic compound. As an available α-amino acid reactant, l-proline extensively used in 1,3-dipolar reactions. A diverse spectrum bioactive spiro fused N-heterocycles obtained through this synthetic approach. In review, we have described use synthesis various spiro- scaffolds.

Language: Английский

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Engaging Isatins and Amino Acids in Multicomponent One-Pot 1,3-Dipolar Cycloaddition Reactions—Easy Access to Structural Diversity

Molecules, Journal Year: 2023, Volume and Issue: 28(18), P. 6488 - 6488

Published: Sept. 7, 2023

Multicomponent reactions (MCRs) have undoubtedly emerged as the most indispensable tool for organic chemists worldwide, finding extensive utility in synthesis of intricate natural products, heterocyclic molecules with significant bioactivity, and pharmaceutical agents. The multicomponent one-pot 1,3-dipolar cycloaddition reactions, which were initially conceptualized by Rolf Huisgen 1960, find application contemporary chemistry. In terms green synthesis, is highly favored owing to its numerous advantages, including high step- atom-economies, remarkable product diversity, well excellent efficiency diastereoselectivity. Among pieces research, fascinating reaction involves utilization azomethine ylides generated from isatins amino acids that can be captured various dipolarophiles. This approach offers a efficient convenient method constructing spiro-pyrrolidine oxindole scaffolds, are crucial building blocks biologically active molecules. Consequently, this review delves deeper into dipolarophiles utilized over past six years.

Language: Английский

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Chemo-/Regio-Selective Synthesis of Novel Functionalized Spiro[pyrrolidine-2,3′-oxindoles] under Microwave Irradiation and Their Anticancer Activity

Molecules, Journal Year: 2023, Volume and Issue: 28(18), P. 6503 - 6503

Published: Sept. 7, 2023

A novel series of nitrostyrene-based spirooxindoles were synthesized via the reaction substituted isatins 1a-b, a number α-amino acids 2a-e and (E)-2-aryl-1-nitroethenes 3a-e in chemo/regio-selective manner using [3+2] cycloaddition (Huisgen) under microwave irradiation conditions. The structure elucidation all done 1H 13C NMR HRMS spectral analysis. single crystal X-ray crystallographic study compound 4l was used to assign stereochemical arrangements groups around pyrrolidine ring spiro[pyrrolidine-2,3'-oxindoles] skeleton. vitro anticancer activity analogs 4a-w against human lung (A549) liver (HepG2) cancer cell lines along with immortalized normal (BEAS-2B) (LO2) shows promising results. Out 23 spiro[pyrrolidine-2,3'-oxindoles], while five compounds (4c, 4f, 4m, 4q, 4t) (IC50 = 34.99-47.92 µM; SI 0.96-2.43) displayed significant lines, six 4k, 41.56-86.53 0.49-0.99) lines. In case these recognized be more efficient selective than standard reference artemisinin 100 µM) chloroquine SI: 0.03). However, none them found active as compared artesunic acid [IC50 9.85 0.76 line IC50 4.09 2.01 line].

Language: Английский

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Polycyclic Pyrazolidines by Tandem Diazomalonate Dipolar Cycloadditions and CpRu‐Catalyzed Carbene Additions

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(43)

Published: May 10, 2024

Thanks to the ability of diazo derivatives react either as 1,3-dipoles and carbenes after dinitrogen extrusion, combinations oxa or aza benzonorbornadienes diazomalonates afford polycyclic pyrazolidines via a three-step sequence (i) highly diastereoselective [3+2]-cycloaddition, (ii) CpRu-catalyzed carbene addition, (iii) second dipolar cycloaddition. Of importance, step (II) represents unique access novel bench-stable N,N-cyclic azomethine imines, which behave effective in combination with electron-poor dipolarophiles. Each proceeds efficiently 3-step process can be performed one-pot yield pyrazolidine excellent overall (90 %).

Language: Английский

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Synthesis of highly functionalized spirooxindole derivatives via multicomponent [3+2] cycloaddition reactions

Elsevier eBooks, Journal Year: 2024, Volume and Issue: unknown, P. 129 - 180

Published: Jan. 1, 2024

Language: Английский

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Microwave-assisted synthesis of pyrrolidinyl-spirooxindoles via tandem 1,3-dipolar cycloaddition and oxidative dehydrogenation

Tetrahedron, Journal Year: 2024, Volume and Issue: 169, P. 134379 - 134379

Published: Nov. 14, 2024

Language: Английский

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