Aminomethylation of Thiourea with Formaldehyde and Cyclic Amines

Three-component condensation of thiourea with equimolar amounts of formaldehyde and morpholine afforded N-(morpholin-4-ylmethyl) derivative, whereas analogous reaction with 2 equiv of formaldehyde and amine gave symmetrical N,N′-bis(morpholin-4-ylmethyl)thiourea. In the condensation of thiourea with piperidine and formaldehyde, only symmetrical N,N′-bis(piperidin-1-ylmethyl)thiourea was isolated, regardless of the reactant ratio.     

5-Arylidene-2-thio-4-oxazolidinones in hydroxy- and aminomethylation reactions

Hydroxymethylation and aminomethylation reactions of 5-arylidene-2-thio-4-oxazolidinones lead to the formation of substitution products at the ring nitrogen atom; this has been attributed to thermodynamic reaction control.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 106–108, January, 1989.     

Aminomethylation of pemoline

Aminomethylation of pemoline with primary amines has given the corresponding oxazolo[3,2-a]-1,3,5-triazines or oxazolo[3,2-a]-1,3,5,7-tetrazocines. When secondary amines were used, the 5-amino- or 3,5-bis(aminomethyl) derivatives were obtained.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1670–1674, December, 1990.The authors thank A. V. Dogadin for obtaining and discussing the PMR spectra.     

Structure of 2-amino-4-thiazolinone and its 2-aryl derivatives in the crystalline state

According to IR spectroscopic analysis, the compounds 2-amino-4-thiazolinone and 2-arylamino-4-thiazolinone exist in the amino form in the crystalline state.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 32–37, January, 1985.     

Tautomerism and methylation of 2-imino-4-imidazolidinones

5-Benzylidenecreatinine and 2-phenylglycocyamidine exist in DMSO-D₆ in the imino form. In basic medium, the two compounds exhibit a dual reactivity with respect to methylating agents, forming N₍₂₎- and N₍₃₎-methyl derivatives.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 62–65, January, 1991.The authors wish to express their gratitude to A. V. Dogadin for running the PMR spectra.     

Reaction of thiourea with formaldehyde and simplest aliphatic diamines

N,N′-Bis(hydroxymethyl)thiourea reacted with propane-1,3-diamine at a molar ratio of 2 : 1 to give 5,5′-propane-1,3-diylbis(1,3,5-triazinane-2-thione), whereas 1,3,5,7,11,13,15,17-octaazatricyclo[15.3.1.1^7,11]-docosane-4,14-dithione was obtained in the reaction with equimolar amounts of the reactants. Tricyclic product was also formed in the three-component condensation of thiourea with formaldehyde and propane-1,3-diamine at a ratio of 1 : 3 : 1. The reactions of N,N′-bis(hydroxymethyl)thiourea with ethane-1,2-diamine (2 : 1) and of thiourea with formaldehyde and butane-1,4-diamine (1 : 2 : 1) afforded 5,5′-(ethane-1,2-diyl)bis(1,3,5-triazinane-2-thione) and 5,5′-(butane-1,4-diyl)bis(1,3,5-triazinane-2-thione), respectively.     

Aminomethylation of Symmetric Dialkylthioureas with Formaldehyde and Amino Acids

Russian Journal of General Chemistry - Condensation of 1,3-dialkylthiourea, formaldehyde, and terminal amino acids (C2, C3, or C4) taken in the 1 : 2 : 1 molar ratio has afforded the terminally...     

Guanidine hydrochloride aminomethylation with formaldehyde and simplest amino acids

Aminomethylation of guanidine hydrochloride with aqueous formaldehyde and simplest amino acids depending on the reagents ratio results in bicyclic hydrochlorides (1: 4: 2) or tricyclic iminium chlorides (1: 6: 3) that in their turn may be converted into internal salts: zwitter-ions or betaines respectively.