N-Aminophthalimide

N-arylmethylideneaminophthalimide: Design, synthesis and evaluation as analgesic and anti-inflammatory agents.[Pubmed:29692241]

Mini Rev Med Chem. 2018 Apr 23. pii: MRMC-EPUB-89941.

BACKGROUND AND OBJECTIVE: N-aryl derivatives of phthalimide and 4-nitro phthalimide have demonstrated cyclooxygenase inhibitory activity. Also they possess an excellent analgesic and anti-inflammatory activity. In this work, a new series of N-arylmethylideneamino derivatives of phthalimide and 4-nitro phthalimide were designed and synthesized. METHODS: The designed compounds were synthesized by condensation of the appropriate aldehyde and N-Aminophthalimide in ethanol at room temperature at PH around 3. Their analgesic and anti-inflammatory activity were evaluated by acetic acid-induced pain test and carrageenan-induced paw edema test in mice and rats, respectively. RESULTS AND CONCLUSION: The details of the synthesis and chemical characterization of the analogs are described. In vivo screening showed compounds 3a, 3b, 3f and 3h were the most potent analgesic compounds. In addition compounds 3a, 3c, 3d, 3e and 3j indicated comparable anti-inflammatory activity to indomethacin as reference drug.

Diastereoselective aziridination of 2-B(pin)-substituted allylic alcohols: an efficient approach to novel organoboron compounds.[Pubmed:22026754]

Org Lett. 2011 Nov 18;13(22):6094-7.

We report that 2-B(pin)-substituted allylic alcohols are good substrates for diastereoselective aziridinations in the presence of PhI(OAc)(2) and N-Aminophthalimide. Under the aziridination conditions, the valuable B-C bond remains intact, affording a variety of novel boron-substituted aziridines in good yields and excellent diastereoselectivities. Oxidation of the aziridine B-C bond enables generation of syn-1,3-aminohydroxy-2-ketones with high diastereoselectivity.

Aryl iodide mediated aziridination of alkenes.[Pubmed:16354070]

Org Lett. 2005 Dec 22;7(26):5801-4.

[reaction: see text] Aryl iodide mediated aziridination of a variety of alkenes with N-Aminophthalimide under mild conditions (m-CPBA, K2CO3, CH2Cl2, 25 degrees C) was achieved in moderate to good yields (up to 94%). By recovering the aryl iodide, a recyclable system is developed with product yield over 79% attained for the aziridination of trans-1,2-diphenylethylene.

Development of electrochemical processes for nitrene generation and transfer.[Pubmed:15675851]

J Org Chem. 2005 Feb 4;70(3):932-7.

An electrochemical strategy for running nitrogen-transfer reactions on chemically inert anode surfaces has been developed. The generation and trapping of highly reactive nitrene-transfer reagents can be accomplished under mild conditions on platinum electrodes. The key factor that accounts for the high levels of chemoselectivity in this process is the phenomenon of overpotential. We have found that molecules that are similar in terms of propensity toward oxidation can be differentiated on the basis of their affinity to a given electrode surface. Thereby, reactive species can be selectively generated in the presence of acceptor molecules of interest. Specifically, a wide range of structurally dissimilar olefins can be transformed into the corresponding aziridines in the presence of N-Aminophthalimide. Likewise, nitrene generation in the presence of sulfoxides leads to their chemoselective transformation into the corresponding sulfoximines. In this paper we discuss the underlying mechanistic foundation of these reactions.

Electrochemical imination of sulfoxides using N-aminophthalimide.[Pubmed:12027627]

Org Lett. 2002 May 30;4(11):1839-42.

[reaction: see text] A novel electrochemical sulfoxide imination process is described. Our approach starts with a highly selective nitrene transfer from N-Aminophthalimide to a variety of sulfoxides. This oxidative treatment is followed by reductive N-N bond cleavage under the controlled current conditions, which leads to a range of parent NH sulfoximines. In addition to solving the challenging problem of removing the N-phthalimido group, the overall process avoids the use of toxic oxidants and metal additives.

Enantioselective aziridination of alkenes with N-aminophthalimide in the presence of lead tetraacetate-mediated chiral ligand.[Pubmed:11922794]

Org Lett. 2002 Apr 4;4(7):1107-9.

[reaction: see text] Reaction of various N-enoyl oxazolidinones 5a-f with N-Aminophthalimide and lead tetraacetate in the presence of camphor-derived chiral ligands provides the desired N-phthalimidoaziridines 6a-f in good to high enantiomeric excess (67-95% ee) at 0 degrees C within 15 min. The absolute stereochemistry of the corresponding aziridine derivatives was established by chemical correlations.

Practical olefin aziridination with a broad substrate scope.[Pubmed:11804478]

J Am Chem Soc. 2002 Jan 30;124(4):530-1.

The present study illustrates the possibility of a rational approach that bypasses the requirement for stoichiometric amounts of toxic oxidants and metal additives (including reagents and catalysts) in organic redox reactions. We describe an aziridination process that delivers a nitrene functionality to olefins from a readily available N-Aminophthalimide. Remarkably, both electron-rich and electron-poor olefins are converted to aziridines with high efficiency. The continuum of applied potentials and the heterogeneous nature of reactions at electrode surfaces allow for the electrochemical discrimination of substrates which have similar redox potentials and therefore cannot be selectively reduced or oxidized using soluble reagents. This selectivity is due to the phenomenon of overpotential, the kinetic inhibition of electron transfer on a particular electrode surface.