1,2,4‐Triazines and Calcium Carbide in the Catalyst‐Free Synthesis of 2,3,6‐Trisubstituted Pyridines and Their D‐, ¹³C‐, and Doubly D₂‐¹³C₂‐Labeled Analogues

Chemistry - An Asian Journal, Journal Year: 2023, Volume and Issue: 18(23)

Published: Oct. 16, 2023

A novel synthetic approach to 2,3,6-trisubstituted pyridines, their 4,5-dideuterated derivatives, 4,5-13 C2 - and doubly-labeled D2 -13 -pyridines has been developed using catalyst-free [4+2] cycloaddition of 1,2,4-triazines in situ generated acetylene or labeled acetylene. Calcium carbide water deuterium oxide were used for the generation dideuteroacetylene. carbide-13 mixture with was applied as 13 -acetylene source.

Language: Английский

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Copper-Catalyzed Synthesis of Benzofuropyrimidoisoindole Derivatives

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(11), P. 3427 - 3427

Published: Jan. 1, 2024

Language: Английский

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Organocatalyzed Double C(sp³)−H Alkylation of Cyclic N‐Sulfonyl Ketimines with 3‐Chloropropiophenones: Selective Access to 2,3,6‐Trisubstituted Pyridines

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(33)

Published: July 11, 2023

Abstract An efficient sequential one‐pot, two‐step pseudo‐four‐component reaction between 3/4‐methyl N ‐sulfonyl ketimines with 3‐chloropropiophenones triggered by DIPEA/NaHCO 3 as a cooperative base and subsequent aza‐cyclization using NH 4 OAc is reported. This transition‐metal‐oxidant‐free technique concocts new C−C/C=C/C=N−C bonds selectively, guaranteeing acceptable yields of 2,3,6‐trisubstituted pyridines possessing ortho ‐hydroxyaryl/benzenesulfonamide propiophenone moieties at C2 C3 positions, respectively. Interestingly, while replacing methyl‐substituents straight alkyl chains ketimines, only monoalkylation happened in situ‐generated vinyl ketones to deliver promising 3‐picoline derivatives. Moreover, the synthetic transmutation prepared pyridine derivative led several important classes pyridocoumarin, 5 H ‐chromenopyridine, di(pyridin‐3‐yl) methane

Language: Английский

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Six-membered ring systems: Pyridines and benzo analogs

Progress in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 309 - 354

Published: Jan. 1, 2024

Language: Английский

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