ISSN:
1434-4475
Keywords:
4-Aminothiomorpholine-1,1-dioxide
;
4-Hydroxy-thiomorpholine-1,1-dioxide
;
Reactivity
;
Synthesis
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Abstract The syntheses of 4-amino-thiomorpholine-1,1-dioxide (12) and 4-hydroxythiomorpholine-1,1-dioxide (11) from 1,4-thioxane-1,1-dioxide (1) by pressureless reaction of1 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 of12 with1 gives N,N′-dithiomorpholine-1,1-dioxide (13). Acylation of12 with monochlorides (30–35), dichlorides of dicarboxylic acids (36–40) and carboxylic acid anhydrides (41–43) proceeds smoothly. Compounds38–43 are cyclic imides. Isocyanates give with12 the expected compounds45–48.12 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 with9 to give the bis quaternization product56. 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 with12 the addition product71; sulfur dioxide is added to11 to thiomorpholine-1,1-dioxide sulfonic acid (72).
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00899678
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