A simple and effective annulation of ynediones and (iso)quinoline -oxides was developed to afford various functionalized pyrrolo[2,1-]isoquinolines and pyrrolo[1,2-]quinolines in moderate to excellent yields. This protocol underwent a tandem [3 + 2] cycloaddition/ring-opening/-nucleophilic addition, which exhibited high regioselectivity, broad substrate tolerance, and atom economy under catalyst-, additive-free, and air conditions. Moreover, indolizine was also successfully prepared using pyridine -oxide.
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http://dx.doi.org/10.1021/acs.joc.0c01932 | DOI Listing |
J Org Chem
January 2025
School of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou, 318000, China.
A three-component reaction of alkenyl thianthrenium salts, cyclopropan-1-ols and DABCO·(SO) under catalyst- and additive-free conditions, is accomplished. This sulfonylation with the insertion of sulfur dioxide works efficiently under very mild conditions, leading to a wide range of 1-substituted vinyl sulfones in moderate to good yields. In this protocol, the scope generality of alkenyl thianthrenium salts and cyclopropyl alcohols is demonstrated.
View Article and Find Full Text PDFChem Commun (Camb)
January 2025
Department of Chemistry, Indian Institute of Technology Bhilai, Durg, Chhattisgarh 491002, India.
We report a two-fold strategy to convert amides to amines in the presence of dimethylamine-borane as the hydrogen source. In the absence of any additive, the formation of the amines resulted from reduction of the amides. On the other hand, in the presence of TMEDA and dimethylamine-borane, tertiary amines were obtained from primary amides in a one-pot fashion.
View Article and Find Full Text PDFOrg Biomol Chem
January 2025
Department of Chemistry, Central University of Punjab, Bathinda, Punjab, 151401, India.
The synthesis of novel quinoline-fused triazolo-azepine derivatives has been reported using an intramolecular 1,3-dipolar azide-alkyne cycloaddition strategy. This method possesses considerable potential to synthesize five- and seven-membered rings in high yields (65-87%) without the necessity of metal catalysts or additives. Additionally, this methodology was applicable to pyridine and tetralone based adducts to afford triazolo-azepine derivatives.
View Article and Find Full Text PDFOrg Biomol Chem
January 2025
Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education; Yunnan Provincial Center for Research & Development of Natural Products; School of Chemical Science and Technology, Yunnan University, Kunming, 650091, P.R. China.
A series of enone-hydrazones were synthesized through the reaction of enaminones with hydrazones under solvent-free, additive-free, and metal-catalyst-free conditions. The target products were obtained in high yields, with outstanding group tolerance, stereoselectivity, and chemical selectivity. In this work, a series of novel enaminone skeleton compounds were synthesized, and deuteration experiments showed that enone-hydrazones have different properties from traditional electron-deficient enketones.
View Article and Find Full Text PDFChem Asian J
January 2025
Department of Chemistry, Indian Institute of Science Education and Research Pune, Dr. Homi Bhabha Road, Pashan, Pune, 411008, India.
We have explored NHSi-supported copper(I) complexes as active and highly efficient catalysts for A (aldehyde-alkyne-amine) and KA (ketone-alkyne-amine) three-component coupling reactions to synthesize propargyl amines in excellent yields with high TOF under solvent-and additive-free conditions.
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