References:
#1:
Weinmann, H.; Harre, M.; Koenig, K.; Merten, E.; Tilstam, U. Tetrahedron 2002, 43, 593-595.
This reference discusses a two-step synthesis of 2-amino imidazole from cyanoamide and a beta-amino ketal. This is very similar to the transformation in our SSG article of molecule 6 to 25 which involves cyanoamide and a beta-amino ketone, instead of a ketal. Scheme 2 (shown below) from the article details a general reaction scheme for this transformation.

Extrapolating from the information in this scheme, we have postulated the mechanism for their transformation to be the following: (1) the amine N of molecule 5 attacks the nitrile C of molecule 4, followed by proton transfers to form compound 6; (2) An SN1 substitution reaction occurs between an –NH2 group and the ketal C, followed by an E1 elimination reaction resulting in the formation of Product 3. The R group in this case as explained in reference can represent either methyl or ethyl.

Our mechanism involves similar steps, in a slightly different order: (1) the amine group of cyanoamide attacks the carbonyl carbon, and proton transfers occur; (2) an amine N attacks the nitrile C in the molecule, followed my more proton transfers; (3) An E1 elimination reaction results in the formation of compound 25.

References citing reference #1:
#1: Safari, J.; Zarnegar, Z. J. Chem. Sci. 2013, 125, 835-841.
This journal reference cited reference 1 because both reference one and this journal reference highlight the importance of maintaining optimal conditions for synthesis of a substituted imidazole. The H2SO4 acts as an acid catalyst to catalyze the synthesis of a substituted imidazole ring.

#2: Hekmatshoar, R.; Jahanbakhshi, H.; Mousavizadeh, F.; Rahnamafar, R. G.U. Journal of Science 2012, 25, 29-34.
This journal article reported the synthesis of a substituted imidazole ring using H2SO4 as an acid catalyst. Both reference 1 and this journal article show that the use of an acid catalyst provides certain conditions that help with the formation of an imidazole ring.

#3: Satyanarayana, V. S. V.; Sivakumar, A. Chem. Pap. 2011, 65, 519–526.
This article cited reference 1 because it used H2SO4 as an acid catalyst in a similar manner to catalyze the synthesis of a substituted imidazole ring. This acid catalysis is necessary to maintain the reaction mixture at an optimal pH that best favors product formation.

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Weinmann, H.; Harre, M.; Koenig, K.; Merten, E.; Tilstam, U. Tetrahedron 2002, 43, 593-595.

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