96308-13-3Relevant academic research and scientific papers
One-pot and regioselective synthesis of polysubstituted 3,4-dihydroquinazolines and 4,5-dihydro-3H-1,4-benzodiazepin-3-ones by sequential Ugi/Staudinger/aza-Wittig reaction
Xiong, Jun,Wei, Xiao,Wan, Yu-Chen,Ding, Ming-Wu
, p. 1072 - 1078 (2019/01/15)
An efficient one-pot and regioselective synthesis of 3,4-dihydroquinazolines and 4,5-dihydro-3H-1,4-benzodiazepin-3-ones by Ugi/Staudinger/aza-Wittig sequence has been developed. The Ugi reactions of 2-azidobenzylamines, aldehydes, acids (or α-keto acids)
Tripod-tripod coupling of triazides with triphosphanes. The synthesis, characterization, and stability in solution of new cage compounds: Chiral macrobicyclic triphosphazides
Alajarin, Mateo,Lopez-Lazaro, Antonia,Vidal, Angel,Berna, Jose
, p. 2558 - 2570 (2007/10/03)
Several examples of a new type of cage compound, chiral macrobicyclic triphosphazides 15, have been prepared by tripod-tripod coupling of tris(2- azidobenzyl)amines with 1,1,1-tris[(diphenylphosphino)methyl] ethane (triphos). The structure determination of C3 or pseudo-C3-symmetric compounds 15 revealed their propellerlike topology, which accounted for their chirality, the rare Z configuration of the three phosphazide units, and a new conformation of the triphos fragment. Compounds 15 decomposed in solution with a phosphane arm-off mechanism, to give rise to complex mixtures instead of the expected tri-λ5-phosphazenes. The stability of 15 in solution was enhanced by the quaternization of the bridgehead nitrogen atom in the form of an N-oxide. Substituents either in the ortho position to the N termini of the phosphazide units or on the benzylic carbon atoms contributed to a decrease in the stability of macrobicycles 15, and in some cases even prevented their preparation.
Synthetic Applications of Bis(iminophosphoranes). One-Pot Preparation of Rigid Bicyclic Guanidines
Molina, Pedro,Alajarin, Mateo,Vidal, Angel
, p. 1687 - 1695 (2007/10/02)
A one-pot synthesis of , , and bicyclic guanidines based on a new method of dihydropyrimido annelation, which involves reaction of bis(iminophosphoranes) with aryl isocyanates or isothiocyanates is described.The method is also applic
Comparison of the Ease of Thermolysis of Ortho-Substituted Phenyl Azides Having α,β or β,γ Imine Functions
Smith, Peter A. S.,Budde, Gregory F.,Chou, Shang-Shing P.
, p. 2062 - 2066 (2007/10/02)
o-Azidobenzaldehyde benzylimine (7) thermolyzes 34 times faster than phenyl azide and 1.6 times faster than p-chlorobenzaldehyde o-azidoanil (8), whereas benzaldehyde (o-azidobenzyl)imine (9) and acetophenone (o-azidobenzyl)imines (10a-e) show little or no rate enhancement over phenyl azide.An electrocyclic mechanism can account for the rates of 7 and 8 relative to each other but not of 8 relative to phenyl azide; 9 and 10a-e appear to thermolyze by nitrene formation, even though a mechanism through intramolecular cycloaddition may in principle be available.A mechanism based on electrostatic effects in a dipolar transition state can corr elate the effects of different types of α,β-unsaturated ortho substituents.
