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Synthesis of 1-Aryl-(1,2-dideoxy-α-d-glucofurano)-[2,1-d]imidazolidine-2-selones and the Crystal Structure of the 1-P-bromophenyl Derivative by José Fernández-Bolaños Guzmán; Troels Skrydstrup; Amparo López-Castro; Ma. Jesús Diánez Millán; Ma. Dolores Estrada de Oya is a Biochemistry, Genetics and Molecular Biology article available to read on EtoBox.

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Although the reaction of 2-amino-2-deoxy sugars with isocyanates and isothiocyanates to give glycofuranoimidazolidin-2-ones and -2-thiones is well known ~'2, no reactions with isoselenocyanates have been reported. We now report the synthesis, in yields of 77-88%, of the crystalline 1-aryl-(1,2dideoxy-c~-D-glucofurano)[2,1-d]imidazolidine-2-selones (1-3) by the reaction of 2-amino-2-deoxy-I>glucose with aryl isoselenocyanates 3 in aqueous ethanol containing 10% of acetic acid. The intermediates 4, which were detected by TLC (see Experimental), are analogous to those isolated in the corresponding reactions with aryl isothiocyanates 2. The rates of formation of bicyclic selones were 2 > 1 > 3, which reflects the inductive effects of the 4-methoxy and 4-bromine substituents, respectively. Compounds 1-3 are similar to chiral oxazolidine-2-selones that have been used 4 for quantitative detection of remote chiral centres using 77Se NMR spectroscopy. The structures 1-3 were assigned on the basis of analytical, UV, IR, ~ H and 13C NMR, and MS data (see Experimental). The tH and 13C NMR data (Tables I andII) are similar to those of the 2-one and 2-thione analogues 2, except that the resonanc

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Author

José Fernández-Bolaños Guzmán; Troels Skrydstrup; Amparo López-Castro; Ma. Jesús Diánez Millán; Ma. Dolores Estrada de Oya

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0008-6215)

Published

1992

Language

EN

Field

Biochemistry, Genetics and Molecular Biology (Life Sciences)