- IMIDATES IN ORGANIC SYNTHESIS: METHYL N-CYANOMETHYLMETHANIMIDATE
-
Synthesis, preliminary properties and reactions of the reagent Methyl N-cyanomethylmethanimidate are reported.
- Hosmane, Ramachandra S.
-
p. 363 - 366
(2007/10/02)
-
- Reagents for Bioorganic Synthesis: Preparation, Properties, and Reactions of Ethyl and Methyl N-(Cyanomethyl)methanimidates
-
An efficient procedure for the preparation of the reagents ethyl and methyl N-(cyanomethyl)methanimidates (NCCH2N=CHOR) (1a, R=Et; 1b, R=Me) is presented,along with their preliminary properties and reactions.The reaction of aminoacetonitrile hydrochloride with trialkyl orthoformate gave 4(5)-imidazolone.The reaction of aminoacetonitrile (free base) with the ortho ester, catalyzed by formic acid, gave methyl N-7H-imidazoimidazol-2-ylmethanimidate (6).The reaction of 1b with 2-aminothiazole and 2-aminopyrimidine, catalyzed by trimethylsilyl triflate, gave 2-(5'-imino-2'-imidazolin-1'-yl)thiazole (9) and 2-(5'-imino-2'-imidazolin-1'-yl)pyrimidine (10), respectively.Compound 10 underwent facile acid hydrolysis to form 2-(formylamino)pyrimidine (11).The reactions of 2-aminothiazole with 2 equiv of 1b or that of 10 with 1 equiv of 1b both provided 2-thiazole (12).
- Hosmane, Ramachandra S.,Burnett, Friedrich N.,Albert, Mitchell S.
-
p. 1212 - 1215
(2007/10/02)
-