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X-ray crystal structures of new chiral enaminones from 2,4-pentanedione and their heterocyclic derivatives

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New chiral enaminones from 2,4-pentanedione (1, 4) and their 1,4-oxazepinium and 1,4-thiazepinium derivatives (5–7) were synthesized and their crystal structures were determined by single crystal X-ray diffraction studies. The crystallographic data for these compounds are as follows: (R)-(1-Methyl-3-oxo-but-1-enylamino)-phenylacetic acid methyl ester (1): a = 7.574(1) Å, b = 12.530(1) Å, c = 14.245(1) Å, P212121. (R)-4-(2-hydroxy-1-phenyl-ethylamino)-pent-3-en-2-one (2): a = 5.543(1) Å, b = 9.433(1) Å, c = 12.237(2) Å, β = 100.687(3)°, P21. (2S, 3R)-3-hydroxy-2-(1-methyl-3-oxobut-1-enylamine) butyric acid methyl ester (3): a = 5.583(1) Å, b = 8.660(1) Å, c = 12.149(1) Å, α = 92.85(1)°, β = 91.00(1)°, γ = 90.16(1)°, P1. (R)-3-[2-Methoxycarbonyl-2-(1-methyl-3-oxo-butylideneamino)-ethyldisulfanyl]-2-(1-methyl-3-oxo-butylideneamino)-propionic acid methyl ester (4): a = 9.309(1) Å, b = 11.460(1) Å, c = 11.310(1) Å, β = 112.582(2)°,P21.(3R)-5,7-dimethyl-3-phenyl-2,3-dihydro-[1,4]oxazepinium trifluoroborate (5): a = 8.958(1) Å, c = 18.085(1) Å, P43. (2S, 3R)-3-methoxycarbonyl-2, 5,7-trimethyl-2, 3-dihydro-[1,4] oxazepin-4-ium trifluroborate (6): a = 8.626(1) Å, b = 11.597(1) Å, c = 13.733(19) Å, P212121. 3-Methoxycarbonyl-5, 7-dimethyl-2, 3-dihydro- [1,4]-thiazepin-4-ium trifluoroborate (7): a = 13.737(1) Å, b = 6.244(1) Å, c = 16.041(1) Å, β = 104.927(2)°, P21/n.

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Acknowledgments

RGE and MCL acknowledge support from CONACYT grants (37821-N, 40950-Q) and DGAPA, UNAM (IN232202); WFR acknowledges support from NSERC, Canada. MCL is grateful for the CONACYT PhD scholarship received during this research.

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Authors and Affiliations

  1. Departamento de sistemas biológicos, UAM-Xochimilco, Calzada del Hueso 1100 Col. Villa Quietud, Coyoacán,, 04960, México,, D. F

    M. Concepción Lozada

  2. Instituto de Química, UNAM, Circuito Exterior, Ciudad Universitaria, Coyoacán, Coyoacán,, 04510,, México, D. F

    Raúl G. Enríquez, Manuel Soriano-García & Rubén A. Toscano

  3. Centro de Química, Instituto de Ciencias, BUAP, Puebla, 72000, México

    Dino Gnecco

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  1. M. Concepción Lozada
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  2. Raúl G. Enríquez
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  3. Manuel Soriano-García
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  4. Rubén A. Toscano
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  5. Dino Gnecco
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Correspondence to Raúl G. Enríquez or Manuel Soriano-García.

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Supplementary material

CCDC-202756, CCDC-202757, CCDC-202759, CCDC-202761, CCDC-202758, CCDC-202760 and CCDC-202762 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/cgi-bin/catreq.cgi, by e-mailing data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK, fax; +44(0)1223–336033.

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Concepción Lozada, M., Enríquez, R., Soriano-García, M. et al. X-ray crystal structures of new chiral enaminones from 2,4-pentanedione and their heterocyclic derivatives. J Chem Crystallogr 37, 119–133 (2007). https://doi.org/10.1007/s10870-006-9163-8

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