57524-14-8Relevant academic research and scientific papers
Stable and reusable nanoscale Fe2O3-catalyzed aerobic oxidation process for the selective synthesis of nitriles and primary amides
Murugesan, Kathiravan,Senthamarai, Thirusangumurugan,Sohail, Manzar,Sharif, Muhammad,Kalevaru, Narayana V.,Jagadeesh, Rajenahally V.
supporting information, p. 266 - 273 (2018/01/12)
The sustainable introduction of nitrogen moieties in the form of nitrile or amide groups in functionalized molecules is of fundamental interest because nitrogen-containing motifs are found in a large number of life science molecules, natural products and materials. Hence, the synthesis and functionalization of nitriles and amides from easily available starting materials using cost-effective catalysts and green reagents is highly desired. In this regard, herein we report the nanoscale iron oxide-catalyzed environmentally benign synthesis of nitriles and primary amides from aldehydes and aqueous ammonia in the presence of 1 bar O2 or air. Under mild reaction conditions, this iron-catalyzed aerobic oxidation process proceeds to synthesise functionalized and structurally diverse aromatic, aliphatic and heterocyclic nitriles. Additionally, applying this iron-based protocol, primary amides have also been prepared in a water medium.
Synthesis and characterization of all-E-(4,4'-13C2)-astaxanthin strategies for labelling the C15-end groups of carotenoids
Jansen, Frans Jos H. M.,Lugtenburg, Johan
, p. 829 - 836 (2007/10/03)
The all-E isomer of (4,4'-13C2)astaxanthin (1a) has been prepared by total synthesis starting from commercially available 99% 13C enriched acetonitrile. The labelled astaxanthin was obtained in high purity and with high isotope incorporation. For this synthesis, the C15 + C10 + C15 strategy was used. The central C10-synthon, 2,7-dimethylocta-2,4,6-triene- 1,8-dial (3), was coupled with 13C-enriched C15-phosphonium salt 2a. The new synthetic scheme for the preparation of the C15-phosphonium salt is discussed in this paper; the same scheme can be used to label all positions and combinations of positions of the C15-phosphonium salt.
The chemistry of thujone. XVI. Versatile and efficient routes to safronitrile, β-cyclogeranonitrile, β-cyclocitral, damascones, and their analogues
Kutney, James P.,Gunning, Philip J.,Clewley, Robin G.,Somerville, John,Rettig, Steven J.
, p. 2094 - 2114 (2007/10/02)
Thujone, a waste by-product of the Canadian forest industry, has been utilized as a starting material to develop a versatile synthetic route to the damascones (rose oil ketones) and related analogues.The synthetic sequence provides a route to β-cyclocitral (45), the latter having been previously converted to β-damascone (2).In addition, thujone-drived intermediates are converted to β-damascenone (48) and to intermediates that can be utilized for the preparation of damascone analogues.In conjunction with the above, an efficient route to safronitrile (42), β-cyclogeranonitrile (43), and β-cyclocitral (45) from 2,6-dimethylcyclohexanone has been developed.In summary, these studies afford an attractive versatile route to these important perfumery materials.
NEW APPROACH TO THE CYCLIZATION OF TERPENOIDS
Kron, A. A.,Burdin, E. A.,Novikov, N. A.,Aul'chenko, I. S.
, p. 1901 - 1904 (2007/10/02)
The cyclization of pseudoionone, geranic acid, and its nitrile in the presence of catalytic amounts of acid at elevated temperature proceeds with high yield, while the corresponding cyclic products are formed predominantly as α-isomers.
A NEW, SPECIFIC SYNTHESIS OF β-CYCLOCITRAL
Picard, Jean-Paul,Nzabamwita, Gaspard,Lacoste, Florence,Calas, Raymond,Dunogues, Jacques
, p. 135 - 140 (2007/10/02)
A new specific synthesis of β-cyclocitral is presented.The key step is the dehydration of the trans 2.2.6-trimethylcyclohexanone cyanohydrin by thionyl chloride.
