86151-02-2Relevant articles and documents
Nitroimidazoles: Part VIII - 2-Amino-1-methyl-5-nitroimidazoles and Derivatives
Sudarsanam, V.,Nagarajan, K.,Arya, V. P.,Kaulgud, A. P.,Shenoy, S. J.,Shah, R. K.
, p. 989 - 996 (2007/10/02)
Treatment of 1-methyl-2-methylsulphonyl-5-nitroimidazole (3) with liquid ammonia gives 2-amino-1-methyl-5-nitroimidazole (2).With sodamide and 3, the major product is the sulphone (4). 2 is transformed by isocyanates into ureas (5a-c), while with 2-chloroethyl isocyanate, imidazolidinone (6) and aminooxazolinone (7) are obtained. 2 is less reactive towards isothiocyanates and gives under forcing conditions, thioureas (8a,b) and guanidines (9a,b).Amides (10a-c) are obtained from 2 by acylation and 10d-g from sulphone (3) by displacement reactions as also sulphamides (11a-c).Cyclic anhydrides and 2 lead to imides (13-15). 2 is transformed into schiff bases (16a-k), some of them being reduced by sodium borohydride to arylalkylamines (17a-c).The ethoxymethylene derivative (18) of 2 is transformed into a large number of formamidines (19a-r), (20a-c) and 21, some of them being further converted into the dichloroacetyl derivatives (22a-c).Reaction of 18 with sodium borohydride affords the ethoxymethylamine (23b) and methylamine derivative (23a).The latter is available from 2 along with dimethylamine by alkylation with methyl iodide.A less satisfactory route for 23a and 23c is displacement of sulphone group from 3 by appropriate amine.Analogous displacements on 3 provide the derivatives 23d,e and 24.The product from the reaction of 3 with sodium azide is the azido derivative (25).The aziridine (27) undergoes iodide-catalysed ring opening to form 29a and does not rearrange to the imidazoline (28).The aminoethanol derivative (29b) results from 27 by an acid-catalysed reaction.
