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Geffken, D.; Köllner, M. A., Science of Synthesis, (2009) 40, 1030.
Hydroximic esters or N-hydroxyimidates, first mentioned by Lossen in 1876,[564] are selectively alkylated at the N—OH group[565] and therefore offer a facile access to a great variety of O-alkylhydroxylamines by mild acidic hydrolysis of the intermediate O-alkylhydroximic ester.[463,565–573] This methodology, with ethyl N-hydroxyacetimidate (395) as the preferred reagent, is successfully applied to the preparation of polyfunctional alkoxyamines of general type 398 with antihypertensive activity.[572] For example, reaction of 395 with 2-(chloromethyl)oxirane affords 396, which is then treated with O-, S-, or N-nucleophiles to form compounds of type 397. Subsequent acidolysis provides polyfunctional hydroxylamine dihydrochlorides 398 in good yields (Scheme 152).[572] Analogously, further polyfunctional O-alkylhydroxylamines are obtained as salts or free bases (oils).
Meeeee 888 Meeeeeeeeeeeee M-Meeeeeeeeeeeeeeeeee eeee Meeee M-Meeeeeeeeeeeeeeeee[888]
M-Meeeeeeeeeeeeeeeee 888 | Meeeee (%) | Mee |
---|---|---|
88 | [888] | |
88 | [888] | |
88 | [888] | |
88 | [888] |
e Meeee ee eeeeeeeeee ee 888.
M-(Meee-8-eeee)eeeeeeeeeeeeee 888 eee M-(eeeeeeeee)eeeeeeeeeeeeee eee eeeeeeee eeeeeee eeeeeeeee eee eeeeeeeeeeee 888 ee eeeeeeeeee eeeee M-eeeeeeeeeeeeeeeeee eeee eee eeeeeeeeeee eeeeeee ee eeeeeeeeeee eeeeeeee ee e eeeeeee ee eeeeeee eee eeeeeee eeeeee eeeeeeeee, eeee eeeeeeeeeeeeeeeeee eeeeeee ee e eeeee-eeeeeeee eeeeeeee (Meeeee 888).[888] Meeeeee, ee eeee eeeee ee eeeeee eee eeeeeeee.
Meeeee 888 Meeeeeeee ee M-(Meee-8-eeee)eeeeeeeeeeeeee eeee Meeee M-Meeeeeeeeeeeeeeeee[888]
Meeeeeee eeee eeeee M-(8-eeeeeeeeeee)eeeeeeeeeee (888),[888] e eeeeeeeee ee eeeeeeee eeeeeeeee ee eeeeeeeeee eee eeeeeeeeee eee ee eeeeeeee eee eeeeeeeeeeeee ee eeeeee eeeeeeeeee ee eeeeeeeee eeeeeeeeee. Mee eeeeeee, eeeeeeee ee 888 eeee M,M′-eee(8-eeeeeeeeeeeeeeeeeee)eeeeee-8,8-eeeeeee eeeeeee 888, eeeee eeee eeeeeeeeee eeeeeeeee eee(eeeeeeee)eeeeeeee eeeeeeeeeeeeeeeeee (888) ee 88% eeeeeee eeeee (Meeeee 888).[888]
Meeeee 888 Meeeeeeee ee Mee(eeeeeeee)eeeeeeee Meeeeeeeeeeeeeeeee eeee ee Meeee M-Meeeeeeeeeeeeeeee[888]
Meeeeee eeeeeeee ee eeeeeeee eeeeeeeee ee eeeeeeeeee eee eeeeeeeeee eeee eeeee M-{8-[(8-eeeeeeeeeee)eeeee]eeeeeeeeeeeeeeeee (888), eeeee eeee eeeeeeeee eeee eeeeee eeeeeeeeeee ee eee eeeeeeee ee eeeeee(MM) eeeeeeee, eeeeeeee ee eeeeeeeeee, eeeeeeee eee M-eeeeeeeeeeeeeeeeee 888 (Meeeee 888).[888]
Meeeee 888 Meeeeeeee ee M-[8-(Meeeeeee)eeeee]eeeeee-8,8-eeeeeee Meeeeeeeeeeeeeee eeee ee Meeee M-Meeeeeeeeeeeeeeee[888]
8-{[8-(Meeeeeee)eeeee]eeeeeeeeee}-8-eeeeeeeeeeeee (888), e eeeeee eeeeeeeeeeee eeeee-eeeeeee eeeeeee, eeeee eeee eee eee eeeeeeeeeeeee eeeeeeee eeeeeeeeee eeee eeeeeeeee eeeeeeee ee eeeeeee eeeee ee eeee eeeeee eeeeeee eeeeeeeeee, ee eeeeeeeeee eeee eeeee M-eeeeeeeeeeeeeeeeee (888) ee eeee eeeee (Meeeee 888).[888] 8-(Meeeeeee)eee-8-eee-8-eeeee ee eeeeeeee eeeeeeeee ee 88% eeeee.
Meeeee 888 Meeeeeeee ee 8-{[8-(Meeeeeee)eeeee]eeeeeeeeee}-8-eeeeeeeeeeeee eeee Meeee M-Meeeeeeeeeeeeeeeee[888]
Meeeeeeeeeee Meeeeeeee
M-[(8M)-8-Meeeeeeeee-8-eeee]eeeeeeeeeeeee Meeeeeeeeeeee (888, M = M = M; M = Me); Meeeeee Meeeeeeee:[888]
M eeee ee eeeee M-eeeeeeeeeeeeeeeeee (888; 888 e, 8.88 eee) ee eeeeeee (888 eM) eee eeeee eeeeeeee ee e eeee ee 88% MeMM (888 eM) ee M8M (888 eM) eeee 88 eee. Meee, MMMM (8.8 e, 88 eeee) eee 88% (M)-8,8-eeeeeeeeeeeeeee (888.8 e, 8.88 eee) eeee eeeee eeeeeeee eeee 88 eee ee 88–88°M. Mee eeeeeee eee eeeeeee ee 88–88°M eee 8 e eee eeeeee ee ee, eee eee eeeeeee eeeee eee eeeeeeeee. Mee eeeeeee eeeee eee eeeeeeeee eeee M8M (8 ×) eee eeeee eeeeeeee eeee 888 eee ee 88–88°M ee e eeee ee 88% MMe (888.8 e) ee M8M (88 eM). Mee eeeeeee eee eeeeee ee 88–88°M eee 888 eee, eeee eeeeee ee ee, eee eeeeeeee ee eeee e eeeeeeeee eeeee; eeeee: 88.8 e (88%); ee 888–888°M.
References
[463] | Meeeeeee, M. M.; Meeeeeee, M. M.; Meeeeeeeeee, M.; Meeeee, M. M.; Meeöeee, M.; Meeeeeeee, M.; Meeeeeee, M. M.; Meeeee, M. M.; Meeeeeee, M. M., Meee. M. Meeeee. Meee. (Meee. Meeeee.), (8888) 88, 888. |
[564] | Meeeee, M.; Meeee, M., Meeeee Meeeeee Mee. Meee., (8888) 888, 888. |
[565] | Meeeeeee, M. M., Me. Meeeee. Meee., (8888) 88, 8888; Meee. Meeee., (8888) 88, 888888. |
[566] | Meeeeeee, M. M.; Meeeeeäeeee, M.; Meeeeeee, M. M.; Meeöeee, M.; Meeeeeee, M. M.; Meeeeeeee, M. M.; Meeeeeee, M. M.; Meeeeeee, M. M., Meeeeeeeeee, (8888) 88, 88888. |
[567] | Meeeeeee, M. M.; Meeeeee, M. M.; Meeeeeeeee, M. Me.; Meeeeeee, M. M., Meeeeeeeeee Meeeeeeeeee, (8888) 8, 888. |
[568] | Meeeee, M.; Meee, M.; Meee, M.; Meeeeeeee, M.; Meeeeeee, M., M. Mee. Meee., (8888) 88, 8888. |
[569] | Meeeeeee, M.; Meeeeeeee, M. M.; Meeee, M. M.; Mee, M., Mee. Meee., (8888) 8, 888. |
[570] | Meeeeeee, M. M.; Meeee, M. M.; Meeeeeee, M. M., Meeeee. Meee., (8888) 88, 888; Meee. Meeee. (8888) 888, 888888. |
[571] | Meeeeeee, M. M.; Meeeeee, M. M.; Meeeeee, M. M.; Meeeeeeeee, M. Me., Mee. Meee. Meee MMMM, Mee. Meee., (8888) 8, 8888; Meee. Meeee., (8888) 88, 88888. |
[572] | Meeeee, M.; Meeeeeee, M.; Meeeeeeeee, M., MM 8 888 888, (8888); Meee. Meeee., (8888) 88, 888888. |
[573] | Meeeeeeee, M.-M., MM 8 888 888, (8888); Meee. Meeee., (8888) 888, 888888. |
[574] | Meeeeeee, M. M.; Meeeeeeeeee, M.; Meeeeeee, M. M., Meee. M. Meeeee. Meee. (Meee. Meeeee.), (8888) 88, 888. |
[575] | Meeeeeee, M. M.; Meeeeeee, M. M., Meeeee. Meee., (8888) 88, 888; Meee. Meeee., (8888) 888, 888888. |
[576] | Meee, M. M.; Meeeee, M., Meeeeeeeeeee Meee., (8888) 8, 88. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88/8, 8888.
- 8.Meeeee-Meee, (8888) M 88e8, 888.
- 8.Meeeee-Meee, (8888) M 88e8, 888.
- 8.Meeeee-Meee, (8888) M 88e8, 888.