Guanidine nitro derivatives

Nitrimines are a relatively minor group of At-nitro compound. The nitro derivatives of guanidine and related compounds are the most important examples of the nitrimine group. 

Flashless and Cool Explosive. See Nitro-guanidine (NGu) under Guanidine and Derivatives... 

Nitro derivatives 245 were prepared in high yields by Michael addition of primary and secondary nitroalkanes 243 to a, -unsaturated carbonyl derivatives 244 in the presence of DBU in acetonitrile or dimethylformamide (83JAP(K)216144 84S226 85JOC3692). Triethylamine or tetramethyl-guanidine as base proved ineffective or less effective than DBU (84S226). 

Diethylaminoethylguanidine, C5H28N4, may be considered as the parent compd of its nitro deriv, although not used to prep it 1,l-Diethyl-3(2-nitraminoethy l)-2-nitro-guanidine or N-(/3-Nitraminoethyl)-N di-eihyl-N -nitroguanidine,... 

Picric acid salts Ammonium picraic Guanidine picratc Danger produced hy picraics Tctra- and pcnia-nitro derivatives of phenol Tctranitruphenol PentanitrophennI Nitro derivatives of cresols 2.4,6-T ri n i t lo-m >creso I Physical properties C hcmical properties... 

The effect of steric hindrance on the rates and kinetic isotope effects for reactions of l-nitro-l-(4-nitrophenyl)alkanes and their deuterated analogues with two bicyclic guanidines of comparable basicity (l,5,7-triazabicyclo[4.4.0]dec-5-ene, TBD, and its 7-methyl derivative, MTBD) in THF has been studied. The results disagree with the notion that deuterium kinetic isotope effects are enhanced by steric hindrance, since for the reactions of MTBD with various carbon acids the KIEs decrease with steric hindrance in the carbon acid but the converse is true for reactions of TBD. 

Terada expanded the phospha-Michael reaction to include diphenyl-phosphites [128]. A novel binaphthol-derived guanidine catalyst promoted the addition in high yields and enantioselectivities (Scheme 73). Functionalizing the external nitrogen with a diphenylmethine moeity enhanced selectivities for a large scope of nitro-olefm derivatives. 

The key starting material of one of the first antagonists, argatroban (30-6), comprises a derivative of arginine itself in which the amine is protected as its tert-butoxycarbonyl derivative and an A-nitro group moderates the basic nature of the guanidine group (30-2). That intermediate is first condensed with the piperidine... 

Evaluation of M30 Propellant Containing Nitro-guanidine Derived from Urea/Ammonia Nitrate Process , ARLCD-TR-78063 (1978) (AD-E 400284) CA 91,195396 (1979) 38) J.W. 

Although there are preliminary data supporting the antitumoral activity of quercetin, the most common flavonoid, in humans in the course of a Phase I clinical trial [189], direct evidence of the anticancer effect of flavonoids is derived almost exclusively from studies performed in animal models as well as studies performed on cultured cell lines, Fig. (2). Most animal studies on gastrointestinal cancer have focused on colon cancer using the azoxymethane (AOM) model in rats or mice [190-197]. There are also available reports on models of cancer of the stomach (induced by benzo[a]pyrene [198] or N-methyl-N-nitro-N-nitro so guanidine [199]), oesophagus (N-methyl-N-amylnitrosamine [200]), and the tongue/oral cavity (methyl-(acetoxymethyl)-nitrosamine [198], 7,12-dimethyl-... 

Now for the synthesis. The nitro compound 75 was made from bromopentane and a nitrite in DMSO, a good solvent for Sn2 reactions, and added to the enone 76, an acetal derived from the diketone 74 with the strong base tetramethyl guanidine 77 as catalyst to give the partly protected form 78 of 73. Now all is ready for the various reductions. 

Similarly, nitro and nitroso derivatives of urea and guanidine have been reduced to semicarbazides and aminoguanidines in acid solution [204,217-219]. In aprotic media (DMF) the primarily formed anion radical of A-nitrosourea gives rise to a self-protonation step the deprotonated substrate cleaves easily into several products [220]. 

Derivation Cooling the reaction products of nitro-guanidine, ammonium chloride, and zinc dust. 

Hexahydrotriazines such as (176), which are useful as insecticides, are synthesized from nitro-guanidine derivatives and 7V-methyl-A -bis(chloromethyl)amine (Equation (34)) <91EUP42894l>. 

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