295. Aliphatic nitro-compounds. Part XVI. Condensation of hydroxymethyldialkylamines with nitro-paraffins

Abstract

Hydroxymethyl derivatives of secondary amines and nitromethane or nitroethane yield, on heating, only nitro-diamines of type I1 (R = H or Me). 1-Nitropropane gives chiefly the nitro-amine (111; R = Et) and a little nitro-diamine (I; R = Et). Nitro-amines (111; R = Me) are prepared from nitroethane and hydroxymethyldialkylamine by carrying out the

Nitro-Mannich Reaction

“…Lambert and Rose investigated the use of this chemistry for selective monoaddition of aminomethanols to nitroethane, which typically undergoes double addition. They successfully performed the monoaddition reaction of diethylaminomethanol with nitroethane (Scheme ) . This was accomplished using equimolar quantities of each reagent and performing the reactions over a short period of time at ambient temperature.…”

The Nitro-Mannich Reaction and Its Application to the Stereoselective Synthesis of 1,2-Diamines

“…Consequently, standard reducing systems invariably gave dibenzylamine as the chief reduction product. Fortunately, samarium diiodide gently reduces the nitro function to our desired primary amine 5 in 62% yield. 15b, Hydrogenolysis of the N -benzyl group of 5 , to give the naked 1,2-diamine, caused many problems due to other sites being susceptible to cleavage. It was at this point that we optimized the reaction conditions using N -(4-methoxybenzyl)imines as the N -4-(methoxybenzyl) (PMB) group could be easily removed using ceric ammonium nitrate (CAN) .…”

Reaction of 1, 3-Di-(1-piperidyl)-2-nitropropane with Thiophenol and Hydrogen Sulfide and Preparation of 5-Nitrohexahydropyrimidin-2-thione

“…The mass spectra were determined on a Shimadzu GC-MS QP -1000 EX instrument. Compounds 1 and 6 were prepared as previously described (16,17) .…”

“…In the present study, we investigated the S-alkylation of thiols with the nitro bis-base (1), and some interesting results were obtained in this direction. Thus, 1,3-di-(1-piperidyl)-2-nitropropane (1) was prepared according to an earlier report (16,17) . The S-alkylation of thiophenol with 1 proceeded in high yield, under mild conditions to give 1,3-di(phenylsulfanyl)-2-nitropropane (2).…”