1067227-75-1Relevant academic research and scientific papers
A divergent synthesis of substituted 2-aminoimidazoles from 2-aminopyrimidines
Ermolat'ev, Denis S.,Van Der Eycken, Erik V.
, p. 6691 - 6697 (2008)
(Chemical Equation Presented) A new divergent and efficient synthesis of substituted 2-aminoimidazoles 5 and 6 has been developed starting from the readily available 2-aminopyrimidines 1 and α-bromocarbonyl compounds 2, using conventional heating or microwave irradiation. Thus, the cleavage of 1,2,3-substituted imidazo[1,2-a]pyrimidin-1-ium salts 4 with hydrazine or secondary amines led to 1,4,5-trisubstituted 2-aminoimidazoles 5, when the hydrazinolysis of 2-hydroxy-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-4-ium salts 3, followed by a novel Dimroth-type rearrangement, resulted in formation of 2-amino-1H-imidazoles 6. The relevant pathway of transformations was identified by characterization of the intermediates.
A concise microwave-assisted synthesis of 2-aminoimidazole marine sponge alkaloids of the isonaamines series
Ermolat'ev,Alifanov,Rybakov,Babaev,Van Der Eycken
experimental part, p. 2083 - 2088 (2009/04/03)
A short and efficient route to 1,4-substituted 2-aminoim-idazole alkaloids starting from the easily accessible 2-alkylami-nopyrimidines and α-bromo aldehydes is reported. The formation of the intermediate imidazo[l,2-a] pyrimidinium salts and subsequent cleavage were facilitated by microwave irradiation. Marine sponge alkaloids preclathridines A, C and isonaamines A, C, D were obtained in high yields using the optimized one-pot two-step procedure. Thieme Stuttgart.
