In this study, an efficient multicomponent one-pot route is described for the DABCO-catalyzed synthesis of tetrazolo[1,5-a]pyrimidines. This synthesis strategy is based on the reaction of malononitrile and aldehydes with 5-aminotetrazole monohydrate using 1,4-diazabicyclo[2.2.2]octane (DABCO) in i-PrOH under reflux conditions. This protocol is a simple, green, and low-cost technique to prepare new compounds with potential medicinal properties.
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http://dx.doi.org/10.1007/s11030-017-9760-9 | DOI Listing |
J Org Chem
October 2024
Instituto de Productos Naturales y Agrobiología, Consejo Superior de Investigaciones Científicas, Avda. Astrofísico Francisco Sánchez 3, 38 206 La Laguna, Tenerife, Islas Canarias, Spain.
A practical and efficient addition of water to readily available activated alkynes delivering divinyl ethers is reported. The reaction proceeds with full atom economy in a very straightforward experimental procedure. Additionally, of all the tertiary amines studied to catalyze the reaction, the best and most efficient is clearly DABCO (1,4-diazabicyclo[2.
View Article and Find Full Text PDFOrg Biomol Chem
June 2024
Dept. of Chemistry, Vellore Institute of Technology Chennai Campus, Vandalur-Kelambakkam Road, Chennai - 600127, Tamil Nadu, India.
A previously elusive organocatalytic protocol for the esterification of amides is disclosed. DABCO (10 mol%) is identified as an effective catalyst for the esterification of -pivaloyl amides. Although -pivaloyl amides are nearly planar (amide bond twist () = 4.
View Article and Find Full Text PDFOrg Biomol Chem
October 2023
Shaanxi Key Laboratory of Chemical Reaction Engineering, College of Chemistry and Chemical Engineering, Yan'an University, Yan'an 716000, China.
A DABCO-catalyzed allylic alkylation of tertiary propargylic alcohol-derived MBH carbonates with nitromethane was developed. A series of substituted 1,4-enynes with an all-carbon quaternary stereocenter were efficiently obtained in moderate to high yields. The synthetic utility of the product was demonstrated by facile synthesis of 1,4-enyne-embedded 2-pyrrolidinones.
View Article and Find Full Text PDFRSC Adv
April 2023
State Key Laboratory of Functions and Applications of Medicinal Plants, School of Pharmacy, and Engineering Research Center for the Development and Application of Ethnic Medicine and TCM (Ministry of Education), Guizhou Medical University Guiyang 550004 People's Republic of China
A rapid and simple method was developed for the synthesis of diarylmethyl thioethers a DABCO-catalyzed 1,6-conjugate addition reaction of -quinone methides (-QMs) with organosulfur reagents. A series of diarylmethyl thioethers were synthesized at 13-85% yields by this method. After that, the antibacterial activities of synthesized diarylmethyl thioethers and their derivatives were evaluated.
View Article and Find Full Text PDFMolecules
March 2023
College of Science, Sichuan Agricultural University, Ya'an 625014, China.
Allylation of -unsubstituted isatin ,'-cyclic azomethine imines with Morita-Baylis-Hillman carbonates in the presence of 1-10 mol% DABCO in DCM at room temperature, rapidly gave -allylated and , -diallylated isatin ,'-cyclic azomethine imine 1,3-dipoles in moderate to high yields. The reaction features mild reaction conditions, easily practical operation, and short reaction times in most cases. Furthermore, the alkylated products were transformed into novel bicyclic spiropyrrolidine oxoindole derivatives through the [3+2] or [3+3]-cycloaddition with maleimides or Knoevenagel adducts.
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