Amine oxides azides

Oxidation of Primary Amines, Oximes, Azides, Isocyanates, or Nitroso Compounds to Nitro Compounds... 

Oxidation of primary amines, oximes, azides, isocyanates, or nitroso... 

Ben2yl azide 1855 and N-benzyloxycarbonylbenzylamine 1859 are both transformed by the cheap polymethylhydrosiloxane (PMHS) 1856, in the presence of (B0C)20 and Pd/C, into 92-94% N-BOC-benzylamine 1857 and the polymer 1858 [81]. (Scheme 12.22). Aromatic and aliphatic amine oxides are readily reduced by 1856/Pd/C into their corresponding amines. Thus, e.g., pyridine-N-oxide 860 and quinohne-N-oxide 877 give pyridine and quinohne in 90 and 92% yield, respectively. Analogously, benzyldimethylamine-N-oxide is converted in 88% yield into free benzyldimethylamine [82]. 

Oxidative cleavage of amines 9-39 Reduction of amides 9-47 Reduction of nitro compounds 9-50 Reduction of nitroso compounds or hydroxylamincs 9-51 Reduction of oximes 9-52 Reduction of azides 9-53 Reduction of isocyanates, isothiocyanates, or N-nitroso compounds 9-55 Reduction of amine oxides 9-59 Reduction of azo, azoxy, or hydrazo compounds... 

Amines from azides. The oxide reagent is converted in situ into BujSnH by a hydrosilane such as PhSiHj to effect the reduction. 

Villalgordo et al. [22, 23] as well as Gayo and Suto [25] developed a strategy to cleave pyrimidines from the solid support. After oxidation of the thioether-linkage 17, aromatic substitution of the sulfonyl unit was performed with different N-nucleophiles as amines and azides to give free amino- or azido-pyrimidines 19 (Scheme 16.5). To demonstrate the stability of the linker, the resin-bound derivatives were subjected to different reactions such as saponification, ester reduction, acid chloride formation or Mitsunobu alkylation. A similar approach was presented later on by Hwang and Gong in the SPOS of 2-aminobenzoxazoles [26]. 

Manganese(tl) complexes,, 3, 9-82 acctylacetonates, 48 acetylides, 14 alcohols, 37 alkoxides, 37 alkyl phosphines, 13 alkyls, 12 amides, 15, 16 amine oxides, 39 amines, 16 amino acids, 43, 62 sulfur containing, 70 ammines, 15 antimony ligands, 31-34 arsenates, 4,5, 46 arsenic ligands, 31-34 arsenic oxides, 39 aryls, 12, 14 azides, 22 binary alkyls, 13 bipyridyl, 24, 25 anions, 25... 

Regioselective epoxide opening in l,2-anhydro-3,4 5,6-di-(9-isopropylidene-D-mannitol (46) to amine or azide constitutes another interesting synthetic pathway to D-fructosamine derivatives." As shown in Scheme 20, this reaction furnishes protected 1-amino-1-deoxy-D-mannitol derivatives 47, which can be subsequently oxidized and deprotected into respective A-substituted 1-amino-1-deoxy-D-fructose. 

Arylation of a wide range of NH/OH/SH substrates by oxidative cross-coupling with boronic acids in the presence of catalytic cupric acetate and either triethyl-amine or pyridine at room temperature in air. The reaction works for amides, amines, anilines, azides, hydantoins, hydrazines, imides, imines, nitroso, pyrazi-nones, pyridones, purines, pyrimidines, sulfonamides, sulfinates, sulfoximines, ureas, alcohols, phenols, and thiols. It is also the mildest method for NIO-vinylation. The boronic acids can be replaced with siloxanes or starmanes. The mild condition of this reaction is an advantage over Buchwald-Hartwig s Pd-catalyzed cross-coupling. The Chan-Lam C-X bond cross-coupling reaction is complementary to Suzuki-Miyaura s C-C bond cross-coupling reaction. 

Recent advances in developing important intermediate aromatic nitro compounds, useful in synthetic organic chemistry, have been reviewed. This article includes topics such as the nitration of aromatic hydrocarbons, aryl boronic acids, aryl halides and pseudohalides, aryl carboxylic acids, and the oxidation of aryl primary amines and azide. ... 

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