Hydrolysis of 7,7-Substituted Derivatives of 3-tert-Butyl-3,4-dihydro-2H-thiazolo-[3,2-a][1,3,5]triazin-6(7H)-one

Abstract

CO 3 solution occurs in two steps: in the first step, cleavage of the tetrahydrotriazine ring occurs; and in the second step, opening of the perhydrooxazine ring occurs.

Mechanism of the recyclization of 2-amino-5-benzylidene-1,3-thiazol-4(5H)-one into derivatives of 2-amino-5-benzylidene-1,5-dihydro-4H-imidazol-4-one

“…In previous work [1], we proposed that the isolation of 2a and 3a or of 2b and 3b from the same reaction mixture is a consequence of a unique Dimroth rearrangement involving aminolytic ring opening a the C (2) -S (1) bond and subsequent parallel recyclization of acyclic intermediate A to give the corresponding aminothiazolinone 2 and aminoimidazolinone 3. Aminolysis of 5-benzylidene-pseudothiohydantoin 1 with opening of the C (2) -S (1) bond in the ring is in accord with experimental findings on the alkaline hydrolysis [2], alcoholysis [3], and aminolysis [4] of derivatives of 2-amino-1,3-thiazol-4(5H)-one (pseudothiohydantoin).…”

“…Although the formation of compounds 2a,b may occur without opening of the heterocycle, i.e., directly from the compound 1 by means of addition-elimination at the C (2) =N (2) bond [2], the formation of 3a,b is possible only as the result of ring opening and subsequent recyclization. In previous work [1], we proposed that the isolation of 2a and 3a or of 2b and 3b from the same reaction mixture is a consequence of a unique Dimroth rearrangement involving aminolytic ring opening a the C (2) -S (1) bond and subsequent parallel recyclization of acyclic intermediate A to give the corresponding aminothiazolinone 2 and aminoimidazolinone 3.…”

2-Amino-5,5-bis(hydroxymethyl)-1,3-thiazol-4(5H)-one and its spirodioxane compounds in the Mannich reaction

“…The bis(hydroxymethyl) derivative of pseudothiohydantoin 1a was prepared as the monohydrate by method [1], compounds 1b,c by [16], the spiro[1,3-dioxan-5,5'(4'H)-1',3'-thiazoles] 2a-e by [2], and compound 6 by [17].…”

Three-Component Condensation of Urea with Formaldehyde and Propane-1,3-diamine or Butane-1,4-diamine

“…The reaction of urea with formaldehyde and amines has been known since the middle of the last century. It has been found that condensation of urea with formaldehyde and primary monoamines result in the formation of 5-R-1,3,5-triazinan-2-ones [2][3][4][5][6][7]. Similar compounds have been prepared by reacting dimethylolurea 2 with amines: the reaction of equimolar amounts of dimethylolurea 2 and ethanolamine afforded 5-(2-hydroxyethyl)-1,3,5-triazinan-2-one [8][9][10], while the reaction of dimethylolurea 2 with ethylenediamine or hexamethylenediamine in a 2 : 1 molar ratio furnished 5,5′-ethane-1,2-diylbis(1,3,5triazinan-2-one) and 5,5′-hexane-1,6-diylbis(1,3,5triazinan-2-one), respectively [9].…”

“…However, three-component condensations of urea 1 with formaldehyde and propane-1,3-diamine or butane-1,4-diamine have not been studied previously. Also, the reaction of urea with 1,3,7,9,13,15,19,21-octaazapentacyclo[19.3.1.1 3,7 .1 9,13 .1 15,19 ]octacosane 4 has not been studied.…”