308. Studies in the azole series. Part XVII. The preparation and cyclisation reactions of aminocyanoacetamide

Nitrogen-15-labeled yeast tRNAPhe: double and two-dimensional heteronuclear NMR of guanosine and uracil ring NH groups

“…(3) a-Amino-a-cyanoacetamide (l5N Labeled) (Cook et al, 1949b). The 15 g of the product of the previous step was dissolved in 25 mL of 2 N KOH and extracted twice with chloroform.…”

The Chemistry of Imidates.

“…to cyclize an imidate of similar type using ammonia(180). Slight modifications of this reaction have led to the formation of aminoimidazoles (amino amides were obtained by direct condensation of imidates or thioimidates with compounds of the type of XLII(77,231,296). the preparation of 4,5dicyano-2-methylimidazole from acetimidate and tetrameric hydrocyanic acid (45), of -aminoketone hydrochlorides with imidates in glacial acetic acid to give a neutral fraction, the oxazole (XLIIIa), and a basic fraction identified as the imidazole (XLIIIb)(85).…”

New C(2)‐substituted 8‐alkylsulfanyl‐9‐phenylmethyl‐hypoxanthines III

“…Further, imidazoles G or H could be annulated to F (R 3 Vol. 42 [5] which, to date, have never been applied to the synthesis of compounds F. The base catalyzed rearrangement of suitably substituted thiazoles to imidazoles was described by Cook et al [6] and Sen et al [7]. Cook at al.…”

“…Cook at al. reported that 5-amino-2-methylamino or 2-allylamino-thiazole-4-carboxamide I (R 4 =CH 3, or CH 2 =CHCH 2 ), prepared from 2-amino-2-cyanoacetamide and methyl or allyl isothiocyanato, can be transposed to 1-methyl or 1-allyl-5-amino-2-thioxo-2,3-dihydro-1H-imidazole-4-carboxamide H (R 4 = CH 3 or CH 2 =CHCH 2 ) [6]. Sen et al, instead, described the condensation of 2-amino-2-cyanoacetamide with 3-diethylamino-propyl-1-isothiocyanate to the corresponding 2-thioxoimidazol H (R=(CH 3 ) 2 N(CH 2 ) 2 CH 3 ) [7].…”