Redox-active molecules as organocatalysts for selective oxidative transformations – an unperceived organocatalysis field

• Elena R. Lopat’eva,
• Igor B. Krylov,
• Dmitry A. Lapshin and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2022, 18, 1672–1695, doi:10.3762/bjoc.18.179

• heterocyclizations. Electrochemical N-ammonium ylide-catalyzed CH-oxidation. Oxidative dimerization of aryl- and alkenylmagnesium compounds catalyzed by quinonediimines. FLP-catalyzed dehydrogenation of N-substituted indolines. Funding This work was supported by the Russian Science Foundation (Grant no. 21-13-00205).

Microwave-assisted synthesis of biologically relevant steroidal 17-exo-pyrazol-5'-ones from a norpregnene precursor by a side-chain elongation/heterocyclization sequence

• Gergő Mótyán,
• László Mérai,
• Márton Attila Kiss,
• Zsuzsanna Schelz,
• Izabella Sinka,
• István Zupkó and
• Éva Frank

Beilstein J. Org. Chem. 2018, 14, 2589–2596, doi:10.3762/bjoc.14.236

• eight tautomeric forms [28], their N(1')-substituted derivatives, lacking a functionality on pyrazole C-4, can only exist in three equilibrating tautomers (OH, CH and NH) [18][29]. Therefore, further heterocyclizations of 4 were performed with monosubstituted hydrazine derivatives. The reaction with

Synthesis of pyrimido[1,6-a]quinoxalines via intermolecular trapping of thermally generated acyl(quinoxalin-2-yl)ketenes by Schiff bases

• Svetlana O. Kasatkina,
• Ekaterina E. Stepanova,
• Maksim V. Dmitriev,
• Ivan G. Mokrushin and
• Andrey N. Maslivets

Beilstein J. Org. Chem. 2018, 14, 1734–1742, doi:10.3762/bjoc.14.147

• intraocular pressure (IOP) [8] etc. (Figure 1). Pyrimido[1,6-a]quinoxalines are one of the most intriguing and unexplored structures representing isosteres of this scaffold. Only few synthetic procedures towards these compounds are described in the literature: heterocyclizations of α-chloroisocyanates with

Nucleophilic dearomatization of 4-aza-6-nitrobenzofuroxan by CH acids in the synthesis of pharmacology-oriented compounds

• Alexey M. Starosotnikov,
• Dmitry V. Shkaev,
• Maxim A. Bastrakov,
• Ivan V. Fedyanin,
• Svyatoslav A. Shevelev and
• Igor L. Dalinger

Beilstein J. Org. Chem. 2017, 13, 2854–2861, doi:10.3762/bjoc.13.277

• ] and its chemistry is being extensively studied (see for example [40][41]). Additional functionality, such as 1,3-dicarbonyl moiety and nitro group, would provide a number of transformations, heterocyclizations, etc. useful for diversification of synthesized derivatives. Conclusion In conclusion

The unexpected influence of aryl substituents in N-aryl-3-oxobutanamides on the behavior of their multicomponent reactions with 5-amino-3-methylisoxazole and salicylaldehyde

• Volodymyr V. Tkachenko,
• Elena A. Muravyova,
• Sergey M. Desenko,
• Oleg V. Shishkin,
• Svetlana V. Shishkina,
• Dmytro O. Sysoiev,
• Thomas J. J. Müller and
• Valentin A. Chebanov

Beilstein J. Org. Chem. 2014, 10, 3019–3030, doi:10.3762/bjoc.10.320

• azoloazine with high chemo- and regioselectivity [11][13][14][15]. In particular, three-component heterocyclizations involving 3-amino-1,2,4-triazoles or 4-substituted 5-aminopyrazoles yielded either 4,5,6,7-tetrahydroazolo[1,5-a]pyrimidine-6-carboxamides under ultrasonication at room temperature (kinetic

• studies on multicomponent heterocyclizations involving different N-containing polynucleophiles and salicylaldehyde are of particular interest due to the bifunctional reactivity of the latter component. The presence of both electrophilic and nucleophilic reaction centers in salicylaldehyde enables

• derivatives from salicylaldehyde, various dicarbonyl compounds, and urea (thiourea) using PdO as a catalyst (Scheme 2). Heterocyclizations involving both, salicylaldehyde and aminoazoles, are intriguing as well. Thus, for example in the course of the study on the application of 3-amino-1,2,4-triazole and

Gold-catalyzed oxycyclization of allenic carbamates: expeditious synthesis of 1,3-oxazin-2-ones

• Benito Alcaide,
• Pedro Almendros,
• M. Teresa Quirós and
• Israel Fernández

Beilstein J. Org. Chem. 2013, 9, 818–826, doi:10.3762/bjoc.9.93

• 3,4-dihydro-2H-1,3-oxazin-2-ones 4 (arising from 6-exo-dig cyclization) were achieved, with the nucleophilic oxygen attacking the central allene carbon atom in each case. This is an interesting result, because the available examples on related metal-catalyzed allene heterocyclizations usually lead to

Features of the behavior of 4-amino-5-carboxamido-1,2,3-triazole in multicomponent heterocyclizations with carbonyl compounds

• Eugene S. Gladkov,
• Katerina A. Gura,
• Svetlana M. Sirko,
• Sergey M. Desenko,
• Ulrich Groth and
• Valentin A. Chebanov

Beilstein J. Org. Chem. 2012, 8, 2100–2105, doi:10.3762/bjoc.8.236

• similar MCRs of numerous other aminoazoles, a change of direction of the heterocyclizations in the case of 4-amino-5-carboxamido-1,2,3-triazole was not observed when microwave or thermal heating was substituted by ultrasonication at ambient temperature. Keywords: 4-amino-5-carboxamido-1,2,3-triazole

• polyfunctional aminoazoles that have been studied in heterocyclization reactions [5][6][7][8][20], derivatives of 4-amino-1,2,3-triazole have been less well investigated. There are only a few examples of their heterocyclizations with β-diketones [21], N-cyanomethaneimidates [22], isocyanates [23], chalcones [24

• ] and derivatives of carboxylic acids [25][26]. The only MCR involving this type of aminoazole was described in our previous publication [27]. In the case of 4-amino-5-carboxamido-1,2,3-triazole, heterocyclizations can proceed in two main ways: “classical” for α-aminoazole direction with participation

When gold can do what iodine cannot do: A critical comparison

• Sara Hummel and
• Stefan F. Kirsch

Beilstein J. Org. Chem. 2011, 7, 847–859, doi:10.3762/bjoc.7.97

• displays the possibility of diverse product creation through the use of either gold- or iodonium-triggered heterocyclizations. Carbocyclizations with 1,5-enynes Within the rapidly developing area of gold-catalysis, enyne cycloisomerizations have been particularly well studied [76][77][78][79][80][81][82

Gold-catalyzed heterocyclizations in alkynyl- and allenyl-β-lactams

• Benito Alcaide and
• Pedro Almendros

Beilstein J. Org. Chem. 2011, 7, 622–630, doi:10.3762/bjoc.7.73

• which rely on the activation of the allene and alkyne component. The mechanism as well as the regio- and stereoselectivity of the cyclizations are also discussed. Keywords: alkynes; allenes; gold; heterocyclizations; β-lactams; Introduction The chemistry of alkynes and allenes has been extensively

• mechanism as well as the regio- and stereoselectivity of the cyclizations are also discussed. Review Gold-catalyzed heterocyclizations in allenyl-β-lactams Aminocyclizations The AuCl3-catalyzed cyclization of 4-allenyl-2-azetidinones affords bicyclic β-lactams [31]. The former were prepared by the selective

• reactions of allenes are well-known in hydroxyallenes, the heterocyclization of alkoxyallenes is not an easy task and still remains a significant challenge. Gold-catalyzed heterocyclizations in alkynyl-β-lactams Aminocyclizations The precious metal-catalyzed formation of benzo-fused pyrrolizinones 19 from N