99450-18-7Relevant academic research and scientific papers
[Omim]Cl/FeCl3-catalyzed cross-dehydrogenative-coupling of 1,4-benzoxazinones with various indoles
Sharifi, Ali,Moazami, Maryam,Abaee, M. Saeed,Mirzaei, Mojtaba
, p. 2471 - 2480 (2020)
A novel C(sp3)–C(sp2) cross-dehydrogenative-coupling procedure was developed for the reaction of benzoxazin-2-ones with indole derivatives. Thus, ionic liquid-mediated coupling of 1,4-benzoxazinone derivatives with indoles were observed in which [Omim]Cl/FeCl3 acted as both the solvent and the catalyst. Under [Omim]Cl/FeCl3-TBHP conditions, derivatives of 1 coupled at room temperature with indoles bearing various substituents to give the target products in good yields and within 0.5–2?h time period. The procedure is relatively environmentally friendly and is applicable to several derivatives of both reactants to access the desired products.
O-H insertion and tandem N-H insertion/cyclization reactions using an iron porphyrin as catalyst with diazo compounds as carbene sources
Mbuvi, Harun M.,Klobukowski, Erik R.,Roberts, Gina M.,Woo, L. Keith
experimental part, p. 284 - 292 (2010/12/19)
Iron(III) tetraphenylporphyrin chloride, Fe(TPP)Cl, efficiently catalyzed the insertion of carbenes derived from methyl 2-phenyldiazoacetates into O-H bonds of aliphatic and aromatic alcohols, with yields generally above 80%. Although the analogous N-H insertions are rapid at room temperature, the O-H insertion reactions are slower and required heating in refluxing methylene chloride for about 8 hours using 1.0 mol.% catalyst. Fe(TPP)Cl was also found to be effective for tandem N-H insertion/cyclization reactions when 1,2-diamines and 1,2-alcoholamines were treated with diazo reagents to give piperazinones and morpholinones and related analogs such as quinoxalinones and benzoxazin-2-ones. This approach provides a new one-pot route for synthesizing these classes of heterocyclic compounds.
A convenient synthesis of 3,4-dihydro-1,4-benzoxazin-2-ones
Zidar, Nace,Kikelj, Danijel
, p. 5756 - 5761 (2008/09/21)
3,4-Dihydro-1,4-benzoxazin-2-one was prepared for the first time by catalytic hydrogenation of 4-benzyl-3,4-dihydro-1,4-benzoxazin-2-one. A simple and efficient synthesis of 4-benzyl- and 4-alkyl-3,4-dihydro-1,4-benzoxazin-2-one derivatives from ethyl 2-(2-hydroxyphenylamino)acetate and aldehydes is described. Some considerations regarding the reactivity of 3,4-dihydro-1,4-benzoxazin-2-ones are given.
