Monatshefte fur Chemie p. 643 - 657 (1981)
Update date:2022-08-05
Topics:
Asinger, Friedrich
Kaussen, Manfred
Gold-Martin, Irmgard
Saus, Alfons
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.
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Doi:10.1039/jr9480001907
(1948)Doi:10.1016/S0040-4039(01)81806-2
(1981)Doi:10.1039/DT9810001572
(1981)Doi:10.1039/c3ce41805g
(2014)Doi:10.1016/j.bmc.2009.04.013
(2009)Doi:10.1021/ja01245a022
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