A three-component synthesis of beta-alkoxy-beta-keto-enamides–flexible precursors for 4-hydroxypyridine derivatives and their palladium-catalysed reactions.
Lechel, Tilman; Dash, Jyotirmayee; Eidamshaus, Christian; Brüdgam, Irene; Lentz, Dieter; Reissig, Hans-Ulrich; Organic & biomolecular chemistry 8 (2010) 3007–3014; doi:10.1039/b925468d

data_7153317
_publ_section_title
;
 A three-component synthesis of beta-alkoxy-beta-keto-enamides--flexible
 precursors for 4-hydroxypyridine derivatives and their
 palladium-catalysed reactions.
;
_journal_issue                   13
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3007
_journal_page_last               3014
_journal_paper_doi               10.1039/b925468d
_journal_volume                  8
_journal_year                    2010
_chemical_formula_sum            'C11 H12 N2 O3'
_chemical_formula_weight         220.23
_chemical_name_common            (E)-N-(2-Methoxy-3-oxobut-1-enyl)picolinamide
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                73.591(5)
_cell_angle_beta                 81.419(5)
_cell_angle_gamma                69.809(5)
_cell_formula_units_Z            2
_cell_length_a                   8.038(5)
_cell_length_b                   8.521(5)
_cell_length_c                   8.678(5)
_cell_measurement_reflns_used    1024
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.45
_cell_measurement_theta_min      2.45
_cell_volume                     534.2(6)
_computing_cell_refinement       'BRUKER SMART'
_computing_data_collection       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'CCD area Detector'
_diffrn_measurement_method       'phi and omega scans with .3 deg in omega'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0402
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6027
_diffrn_reflns_theta_full        30.55
_diffrn_reflns_theta_max         30.55
_diffrn_reflns_theta_min         2.45
_diffrn_standards_interval_time  '5 sec/frame'
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             232
_exptl_crystal_size_max          .5
_exptl_crystal_size_mid          .19
_exptl_crystal_size_min          .15
_refine_diff_density_max         0.627
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         3200
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0675
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1153P)^2^+0.0220P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1872
_refine_ls_wR_factor_ref         0.2042
_reflns_number_gt                2146
_reflns_number_total             3200
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b925468d.txt
_cod_data_source_block           orgda7m
_cod_database_code               7153317