79207-32-2Relevant academic research and scientific papers
Concerning the Reactivity of Unsubstituted and Alkyl Substituted Thiomorpholines, 5. On the Joint Action of Elementary Sulfur and Gaseous Ammonia on Ketones, 95
Asinger, Friedrich,Kaussen, Manfred,Gold-Martin, Irmgard,Saus, Alfons
, p. 643 - 657 (2007/10/02)
The syntheses of 4-amino-thiomorpholine-1,1-dioxide (12) and 4-hydroxy-thiomorpholine-1,1-dioxide (11) from 1,4-thioxane-1,1-dioxide (1) by pressureless reaction of 1 with hydrazine hydrate and hydroxylamine, resp. is described.In analogy various other N-substituted thiomorpholine-1,1-dioxides are obtained with prim. amines (2-8) and diamines (9,10). 12 condensates with aldehydes (14-24) and ketones (25-29); reaction of 12 with 1 gives N,N'-dithiomorpholine-1,1-dioxide (13).Acylation of 12 with monochlorides (30-35), dichlorides of dicarboxylic acids (36-40) and carbo xylic acid anhydrides (41-43) proceeds smoothly.Compounds 38-43 are cyclic imides.Isocyanates give with 12 the expected compounds 45-48. 12 reacts with chlorinated 1,3,5-triazines to compounds which can be purified only with difficulty (49-51).Quaternization of the N-substituted thiomorpholine-1,1-dioxides with benzylbromide (52,53) and methyliodide (54,55) is possible.Ethylenbromide reacts with 9 to give the bis quaternization product 56.Further reactions of thiomorpholine-1,1-dioxide (57) with sulfuryl chloride (58), bromo cyanide (59), allylic chloride (60), chloro acetonitrile (61) and trityl chloride (62) are described. 11 reacts with carboxylic acid chlorides (63-65) and iso-cyanates (66-70) to yield the expected compounds.Propylene oxide gives with 12 the addition product 71; sulfur dioxide is added to 11 to thiomorpholine-1,1-dioxide sulfonic acid (72). - Keywords: 4-Aminothiomorpholine-1,1-dioxide; 4-Hydroxy-thiomorpholine-1,1-dioxide; Reactivity; Synthesis.
