31385-27-0Relevant academic research and scientific papers
Synthesis of benz[d]oxazolones involving concomitant acetyl migration from oxygen to nitrogen
Ray, Sibdas,Ghosh, Sukla
experimental part, p. 2377 - 2388 (2010/09/07)
Heating of o-acetoxybenzoyl azides 6-10 in toluene leads to the Curtius reaction, which, when followed by closure of oxazolone ring with concomitant migration of acetyl group from oxygen to nitrogen, produces 3-acetoxybenz[d] oxazol-2(3H)-ones 11-15, which undergo hydrolysis with hot dilute hydrochloric acid to furnish benz[d]oxazol-2(3H)-ones 17-21. Thermal reaction of 2-hydroxy-5-nitrobenzoyl azide (22) in toluene finally yields a mixture of 5-nitrobenz[d]oxazol-2(3H)-one (20) and 5-nitrobenz[d]isoxazol-3(2H)-one (23). Copyright Taylor & Francis Group, LLC.
Catalytic aza-Wittig cyclizations for heteroaromatic synthesis
Marsden, Stephen P.,McGonagle, Alison E.,McKeever-Abbas, Ben
supporting information; experimental part, p. 2589 - 2591 (2012/09/08)
The first examples of heterocycle synthesis by iminophosphorane formation/intramolecular aza-Wittig cyclizations that are catalytic in the organophosphorus component are reported. The reaction has been demonstrated in the synthesis of both azine (phenanthridine) and azole (benzoxazole) heterocycles. Catalyst loadings down to 1 mol % have been used with little or no loss in reaction efficiency. The intimate involvement of the phosphine oxide in the catalytic cycle has been verified by in situ infrared spectroscopy.
Novel antitumor 2-cyanoaziridine-1-carboxamides
Iyengar, Bhashyam S.,Dorr, Robert T.,Alberts, David S.,Hersh, Evan M.,Salmon, Sydney E.,Remers, William A.
, p. 510 - 514 (2007/10/03)
A set of 20 2-cyanoaziridine-1-carboxamides was synthesized from 2- cyanoaziridine and appropriate isocyanates. These compounds were active against a variety of solid and hematological tumor cells in culture, including strains resistant to doxorubicin and mitoxantrone. Their potencies in these assays correlated with the lipophilicity of substituents. The N- phenyl derivative was more potent and equally effective to imexon, a cyclized 2-cyanoaziridine-1-carboxamide of clinical interest, against cloned fresh human tumors.
Synthesis of 2-Methyl-4H-1,3-benzoxazin-4-ones and Related Compounds
Stegmann, Hartmut B.,Klotz, Dieter,Weiss, Joachim E.
, p. 4632 - 4636 (2007/10/02)
4H-1,3-benzoxazin-4-ones 2 are smoothly prepared via (acylimino)phosphoranes 1 by intramolecular condensation analogous to a Wittig reaction.Tert. phosphanes are used for the preparation of the (acylimino)phosphoranes 1 which are converted into the corresponding benzoxazines and tert. phosphane oxides, e.g. 2-methyl-4H-1,3-benzoxazin-4-one (2a) which, in spite of some attempts, has not been obtained before.
