Synthesis, structure and rearrangement of iodinated imidazo[1,2-c]pyrimidine-5(6H)-ones derived from cytosine

• Published in: Tetrahedron Vol. 71; no. 1; pp. 27 - 36
• Main Authors: Jansa, Josef, Lyčka, Antonín, Růžička, Aleš, Grepl, Martin, Vaněček, Jan
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 07.01.2015; Elsevier
• Subjects: acids; Atomic structure; chemical structure; Chemistry; Chemistry, Organic; Cytosine; Dimroth-type rearrangement; Imidazole; Imidazopyrimidines; Iodination; iodine; N-Iodosuccinimide; NMR spectroscopy; nuclear magnetic resonance spectroscopy; Physical Sciences; Science & Technology; Spectra; Tetrahedrons; Three dimensional; X-radiation; X-rays; Iodination; N-Iodosuccinimide; Cytosine; Imidazopyrimidines; NMR spectroscopy; Dimroth-type rearrangement; DOUBLE-HELICAL POLYNUCLEOTIDE; ANTI REARRANGEMENT; CROSS-COUPLING REACTION; MOLECULAR-STRUCTURE; SYN; HALOGEN; BOND COVALENT RADII; X-RAY; DERIVATIVES

We describe mild and selective iodination of various 8-substituted imidazo[1,2-c]pyrimidine-5(6H)-ones (ethenocytosines). Starting ethenocytosines were obtained by cyclization of 5-halogenocytosines with chloroacetaldehyde or by subsequent Suzuki–Miyaura cross-coupling between 8-iodoimidazo[1,2-c]py...