Passerini oxidation

Coustier, R, J. Hill, S. Passerini, and W.H. Smyrl. 1998. Silver-doped vanadium oxides as host materials for lithium intercalation. Electrochem. Soc. Proc., 98-16 350-355. 

Jacobs BR, Brilli RJ, Ballard ET, Passerini DJ, Smith DJ. 1998. Aerosolized soluble nitric oxide donor improves oxygenation and pulmonary hypertension in acute lung injury. Am. J. Respir. Crit. Care Med. 158 1536-42... 

Jacobs BR, Smith DJ, Zingarelli B, Passerini DJ, Ballard ET, Brilli RJ. 2000. Soluble nitric oxide donor and surfactant improve oxygenation and pulmonary hypertension in porcine lung inj ury. Nitric Oxide 4 412-22... 

Brilli RJ, Krafte-Jacobs B, Smith DJ, Passerini D, Moore L, Ballard ET. 1998. Aerosolization of novel nitric oxide donors selectively reduce pulmonary hypertension. Crit. Care Med 26 1390-96... 

Owens, B.B., Passerini, S. and Smyrl, W.H. (1999) Lithium ion insertion in porous metal oxides. Electrochim. Acta, 45, 215-224. 

A Passerini-3CR approach has also been used for the synthesis of macrocycles using the same MiBs concept. Scheme 5.21 shows an example of oxidative double P-3CR using a diacid and a diol as bifunctional substrates. Simply heating a THF solution of N-Boc-glutamic acid (72), triethylene glycol (73) and tert-butyl isocyanide in the presence of IBX afforded the macrolide 74 in 44% yield [41]. In this reaction, triethylene glycol (73) was oxidized in situ to the unstable dialdehyde, which then participated in the double P-3CR [42]. 

L. Passerini, and V. M. Goldschmidt and co-workers studied the solid soln. with alumina, and with ferric oxide q.v.). W. Muller said that the oxide prepared by reducing potassium chromate with dry—not moist—hydrogen chloride is quite different from the ordinary oxide, being greyish-green, composed of tube-like plates of the hardness of graphite. 

L. Passerini found that chromic oxide forms a series of solid soln. when it is heated with alumina, but no aluminium chromite is formed the lattice constants of the solid soln. range from a=4-950 A. for Cr203 to 4-740 A. for AI2O3, and c=6-806 A. to... 

The IBX-mediated oxidative Ugi-type multicomponent reaction of tetrahydroisoquinoUne with isocyanides and carboxylic acids affords the nitrogen- and carbon-functionalized tetrahydroisoquinolines 867 in good to excellent yields [1184]. Likewise, the three-component Passerini reaction of an alcohol, carboxylic acid and an isonitrile in the presence of IBX affords the corresponding a-acyloxy carboxamides 868 in generally high yields (Scheme 3.347) [1185]. 

Wetjen M, Kim GT, Joost M, Winter M, Passerini S. Temperature dependence of electrochemical properties of cross-linked poly (ethylene oxide)/lithium bis(trifluoromethane-sulfonyl)imide/n-butyl-n-methylpyrrolidinium bis(trifluoromethanesulfonyl)imide solid polymer electrolytes for lithium batteries. Electro-chimica Acta 2013 87 779-87. 

Paal-Knorr Pyrrole Synthesis Parham Cyclization Passerini Reaction Patemo-Biichi Reaction Pauson-Khand Reaction Payne Rearrangement Pechmann Condensation Pechmann Pyrazole Synthesis Pellizzari Reaction Pelouze Synthesis Periodic Acid Oxidation Perkin Alicyclic Synthesis Perkin Reaction Perkin Rearrangement Perkow Reaction Peterson Reaction... 

F. Decker, S. Passerini, R. Pileggi, and B. Scrosati [1992] The Electrochromic Process in Non-Stoichiometiic Nickel Oxide Thin Film Electrodes. Electrochim. Acta 37, 1033-1038. 

There are many examples of Passerini-tj e reactions mediated by Lewis acids with TiCU having the most widespread use. Passerini-type reactions using TiCU are compatible with a variety of functional groups as can be seen in the nearly quantitative reaction of a-isocyano phosphonate ester 25 with benzaldehyde. An examination of TiCU-mediated diastereoselective Passerini reaction failed to show any clear stereoselection with chiral isocyanide 26 among many other cases. Weaker Lewis acids such as SiCL can also mediate Passerini-twe reactions, but effectively do so only in the presence of a Lewis base. Demnark demonstrated that a-hydroxyamides, such as 27, could be formed in good yields, by using Lewis bases such as pyridine-7V-oxide to activate the SiCU-... 

Many protease/peptidase inhibitor peptidomimetics include a-ketoamide moieties as key bioactive functionalities and the Passerini reaction provides a facile entry for their preparation through the oxidation of a-hydroxy amides. Researchers at Schering-Plough have utilized this strategy to synthesize a variety of a macrocyclic a-ketoamides towards the development of Hepatitis C virus (HCV) NS3 protease inhibitors. Aldehyde 56 was treated with allylisocyanide and acetic acid to give a-acyloxyamide... 

In this context, Zhu and coworkers envisioned the great utility of alcohols in Passerini reaction instead of aldehydes, which are unstable and sometimes difficult to handle, since the carbonyl compounds can be obtained by direct oxidation of the corresponding alcohols. Thus, the authors generated in situ the aldehydes by oxidation of the alcohols 29 using IBX to obtain a-acyloxycarboxamide derivatives 30 in good yields (Scheme 8.10) [22]. 

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