4,6-Diamino-2-morpholino-5-nitrosopyrimidine: a polarized molecular structure within hydrogen-bonded sheets

García, Angélica; Insuasty, Braulio; Cobo, Justo; Glidewell, Christopher

doi:10.1107/s0108270109041122

Cited by 2 publications

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“…pyridine (Dahlgren et al, 2012;Horton et al, 2012;Huth et al, 2007;Klauschenz et al, 1994;Li et al, 2014, Reck et al, 1992 or pyrimidine (Cheprakova et al, 2014;García et al, 2009;Gorbunov et al, 2013;Hansen & Geffken, 2012;Vinogradova et al, 2016). For pyrazine as the heterocycle, however, (to the best of our knowledge and after conducting a database search, see x4) the present work constitutes the first structural report even though the title compound itself has been known since 1969 (Abe et al, 1969).…”

Section: Figurementioning

confidence: 77%

Crystal structure of 4-(pyrazin-2-yl)morpholine

2018

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The molecular structure of the title compound, C 8 H 11 N 3 O, is nearly planar despite the chair conformation of the morpholine moiety. In the crystal, the molecules form sheets parallel to the b axis, which are supported by non-classical hydrogen-bonding interactions between C-H functionalities and the O atom of morpholine and the 4-N atom of pyrazine, respectively. The title compound crystallizes in the monoclinic space group P2 1 /c with four molecules in the unit cell. Chemical contextThe potential applications of aryl and heteroaryl amines in chemistry, materials science and pharmaceutical industries encourages research into the formation of C-N bonds (Rappoport, 2007;Lawrence, 2004, Weissermel & Arpe 1997. N-Heteroarylmorpholine moieties are prevalent in biologically active molecules such as medicines for the treatment of schizophrenia or type-2 diabetes mellitus (Bartolomé -Nebreda et al., 2014). In this context we are engaged in the synthesis of a library of heterocyclic amine derivatives. In course of these investigations, pure crystalline 4-(pyrazin-2-yl)morpholine was isolated with the crystals being obtained upon purification by column chromatography. Structural commentary4-(Pyrazin-2-yl)morpholine (Fig. 1) crystallizes in the monoclinic space group P2 1 /c with four molecules in the unit cell. There are reports in the literature of the molecular structures of compounds in which the morpholine nitrogen atom is coupled to the carbon atom of a non-annelated N-heterocyclic ISSN 2056-9890 Figure 1 The molecular structure of the title compound, showing the atom labelling and 50% probability displacement ellipsoids.

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Section: Figurementioning

confidence: 77%

Crystal structure of 4-(pyrazin-2-yl)morpholine

2018

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“…It has been noted previously that highly polarized electronic structures occur in a wide variety of amino-substituted nitrosopyrimidines (e.g. Quesada et al, 2002Quesada et al, , 2004Melguizo et al, 2003;García et al, 2009; Yé pes et al, 2012) and that this polarization is associated with extensive charge-assisted (Gilli et al, 1994) hydrogen bonding, leading to a wide variety of supramolecular aggregation, ranging from finite aggregates to three-dimensional framework structures.…”

Section: Resultsmentioning

confidence: 99%

A concise synthesis of a highly substituted 6-(1H-benzimidazol-1-yl)-5-nitrosopyrimidin-2-amine: synthetic sequence and the molecular and supramolecular structures of one product and two intermediates

et al. 2018

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A concise and efficient synthesis of 6-benzimidazolyl-5-nitrosopyrimidines has been developed using Schiff base-type intermediates derived from N-(2-aminophenyl)-6-methoxy-5-nitrosopyrimidine-2,4-diamine. 6-Methoxy-N-{2-[(4-methylbenzylidene)amino]phenyl}-5-nitrosopyrimidine-2,4-diamine, (I), and N-{2-[(ethoxymethylidene)amino]phenyl}-6-methoxy-5-nitrosopyrimidine-2,4-diamine, (III), both crystallize from dimethyl sulfoxide solution as the 1:1 solvates CHNO·CHOS, (Ia), and CHNO·CHOS, (IIIa), respectively. The interatomic distances in these intermediates indicate significant electronic polarization within the substituted pyrimidine system. In each of (Ia) and (IIIa), intermolecular N-H...O hydrogen bonds generate centrosymmetric four-molecule aggregates. Oxidative ring closure of intermediate (I), effected using ammonium hexanitratocerate(IV), produced 4-methoxy-6-[2-(4-methylphenyl-1H-benzimidazol-1-yl]-5-nitrosopyrimidin-2-amine, CHNO, (II) [Cobo et al. (2018). Private communication (CCDC 1830889). CCDC, Cambridge, England], where the extent of electronic polarization is much less than in (Ia) and (IIIa). A combination of N-H...N and C-H...O hydrogen bonds links the molecules of (II) into complex sheets.

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4,6-Diamino-2-morpholino-5-nitrosopyrimidine: a polarized molecular structure within hydrogen-bonded sheets

Cited by 2 publications

References 19 publications

Crystal structure of 4-(pyrazin-2-yl)morpholine

Crystal structure of 4-(pyrazin-2-yl)morpholine

A concise synthesis of a highly substituted 6-(1H-benzimidazol-1-yl)-5-nitrosopyrimidin-2-amine: synthetic sequence and the molecular and supramolecular structures of one product and two intermediates

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