Nanoparticulate Copper(II) Oxide Catalyzed Synthesis of Guanidine Derivatives and Their Conversion into Functionalized Iminoguanidines

Yavari, Issa; Sodagar, Esmat; Nematpour, Manijeh; Askarian-Amiri, Mohammad

doi:10.1055/s-0034-1380349

Cited by 8 publications

(4 citation statements)

References 12 publications

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“…The guanylations of secondary, aromatic, or sterically crowded amines cannot be achieved satisfactorily without a catalyst, owing to their decreased nucleophilicity . The d- and f-block metal complexes, as well as the coordination compounds of electron-deficient main-group metals (Li, Al, Mg, and Al) and nanoparticles prepared from transition metal oxides are reported to catalyze most of the guanylation reactions.…”

Section: Introductionmentioning

confidence: 99%

Lithium and Dilithium Guanidinates, a Starter Kit for Metal Complexes Containing Various Mono- and Dianionic Ligands

et al. 2020

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Comparative studies of the synthesis of lithium guanidinates via nucleophilic addition of lithium amides to carbodiimides were performed. Four combinations of small or sterically crowded carbodiimide and sterically crowded lithium amide or lithium amide containing an adjacent amino donor group give ten different types of complexes. In particular, 2,6-[(CH 3 ) 2 CH] 2 C 6 H 3 NHLi (DipNHLi, 1) reacts with (CH 3 ) 2 CHNCNCH(CH 3 ) 2 upon the formation of the dissymmetric dimeric complex 2 with four-coordinate Li atoms. In contrast, 1 with DipNCNDip gives the mononuclear lithium guanidinate 3 with two-coordinate lithium by κ 1 -guanidinate, solvent molecule, and additional interaction with a π-electron cloud of one of the Dip groups. Analogous reactions of 2-[(CH 3 ) 2 NCH 2 ]-C 6 H 4 NHLi (7) yield complexes 8 and 9, where the adjacent amino donors are always coordinated. Further deprotonation of 2, 3, 8, and 9 leads to dilithium guanidinates(2−)4, 5, 10, and 11, among which only 5, containing three Dip groups, is monomeric with contacts to two π-electron systems of Dip groups. The rest of the complexes are tetranuclear with different structural patterns. In the central parts of molecules, toward which the nitrogen atoms of the guanidinates are oriented, lithium atoms are usually pseudotetrahedral, but trigonal in peripheral parts. Adjacent solvent molecules, chelating amino groups, and π-electron systems of Dip groups are coordinated in order to complete coordination polyhedra. Complexes 4 and 5 deoligomerize in solution upon the formation of fluxional monomeric dilithium species. Conversely, 11 is a dimer in solution due to the strong donation of an amino group. The silylated lithium amide {2-[(CH 3 ) 2 NCH 2 ]C 6 H 4 }[(Si(CH 3 ) 3 ]NLi (12) reacts with both carbodiimides to give dinuclear 13 obtained from diisopropylcarbodiimide and monomeric 14 from the second carbodiimide. Complexes 13 and 14 structurally resemble 8 and 9, with the highest degree of the localization of π-electron density within the N 3 C guanidinate system, η 3 -contact to the Dip ring, and a lack of the solvent molecule in 14.

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Section: Introductionmentioning

confidence: 99%

Lithium and Dilithium Guanidinates, a Starter Kit for Metal Complexes Containing Various Mono- and Dianionic Ligands

et al. 2020

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“…The resulting spiro compounds 35 (10 examples) bearing the 1,3-oxazine heterocycle, were obtained in overall very good yields (70–85% yield) (Scheme 12 ), under catalyst-free conditions. 42…”

Section: Synthesis Of New Tryptanthrin Derivativesmentioning

confidence: 99%

Tryptanthrin and Its Derivatives in Drug Discovery: Synthetic Insights

2022

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Tryptanthrin is a golden-yellow, naturally occurring alkaloid that can be obtained from multiple sources and through different synthetic methodologies. This tetracyclic compound displays several relevant biological activities. The potential of this tetracyclic alkaloid has been widely explored, and several researchers have focused their attention on expanding the variety of tryptanthrin derivatives by using a range of synthetic strategies. In this short review, we aim to address recent developments in the synthesis of the tryptanthrin core, as well as the development of new strategies employed by synthetic organic chemists to obtain novel tryptanthrin derivatives with potential biological activity, using different tools from the chemists’ toolbox, such as photocatalysis, solvent-free approaches, and multicomponent reactions.

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“…After 6 hours, the products were isolated with high diastereoselectivities (≥19:1) and high yields (70–83%). 43…”

Section: Synthesis Of Spirocyclic Compoundsmentioning

confidence: 99%

Acetylenic Esters in Organic Synthesis

Hajinasiri¹

2022

Synlett

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Activated acetylenic substrates such as acetylenic esters and alkyl propiolates are very important in organic synthesis. Due to their electron deficiency, these compounds are widely used in combinatorial and multicomponent reactions, enabling the synthesis of a large variety of novel compounds. In addition, these substrates are powerful Michael acceptors and convenient dienophiles and dipolarophiles in Diels–Alder and 1,3-dipolar cycloaddition reactions. The addition of different nucleophiles, primarily phosphorus, nitrogen or sulfur, to the triple bonds of these substrates produces key intermediates, such as Tebby and Huisgen zwitterions, which can lead to designing pathways toward the generation of spirocyclic and polycyclic compounds. This account highlights recent studies on the chemistry of acetylenic esters and their applications in organic synthesis.1 Introduction2 Synthesis of Acyclic and Monocyclic Compounds3 Synthesis of Spirocyclic Compounds4 Synthesis of Polycyclic Compounds5 Conclusion

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Nanoparticulate Copper(II) Oxide Catalyzed Synthesis of Guanidine Derivatives and Their Conversion into Functionalized Iminoguanidines

Abstract: A simple synthesis of functionalized iminoguanidines from N-sulfoketenimines and N,N′,N′′-trisubstituted guanidines, generated by nanoparticulate copper(II) oxide-catalyzed hydroamination of di(cyclo)alkylcarbodiimides, is described.

Cited by 8 publications

References 12 publications

Lithium and Dilithium Guanidinates, a Starter Kit for Metal Complexes Containing Various Mono- and Dianionic Ligands

Lithium and Dilithium Guanidinates, a Starter Kit for Metal Complexes Containing Various Mono- and Dianionic Ligands

Tryptanthrin and Its Derivatives in Drug Discovery: Synthetic Insights

Acetylenic Esters in Organic Synthesis

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