An expedient and divergent tandem one-pot synthesis of pyrimidin-2,4-diones using the Blaise reaction intermediate.
Chun, Yu Sung; Xuan, Zi; Kim, Ju Hyun; Lee, Sang-gi; Organic letters 15 (2013) 3162–3165; doi:10.1021/ol401389j

data_1556197
_publ_section_title
;
 An expedient and divergent tandem one-pot synthesis of
 pyrimidin-2,4-diones using the Blaise reaction intermediate.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              3162
_journal_page_last               3165
_journal_paper_doi               10.1021/ol401389j
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C18 H16 N2 O2'
_chemical_formula_weight         292.33
_chemical_name_common            'U-5 Dr Jun'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 102.5580(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1596(3)
_cell_length_b                   9.7432(3)
_cell_length_c                   13.8929(4)
_cell_measurement_reflns_used    9941
_cell_measurement_temperature    150.(2)
_cell_measurement_theta_max      28.2661
_cell_measurement_theta_min      2.5741
_cell_volume                     1474.44(7)
_computing_cell_refinement       'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_data_collection       'Bruker APEX-II'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_sigmaI/netI    0.0092
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            25573
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.213
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3644
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0395
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0577P)^2^+0.5002P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1098
_reflns_number_gt                3365
_reflns_number_total             3644
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol401389j_si_002.cif
_cod_data_source_block           I
_cod_database_code               1556197