Efficient One-Pot Synthesis of 2,3-Dihydropyrimidinthiones via Multicomponent Coupling of Terminal Alkynes, Elemental Sulfur, and Carbodiimides
Zitao Wang; Yang Wang; Wen-Xiong Zhang; Zhaomin Hou; Zhenfeng Xi; Journal of the American Chemical Society 131 (2009) 15108–15109; doi:10.1021/ja9069419

data_4105207
_publ_section_title
;
 Efficient One-Pot Synthesis of 2,3-Dihydropyrimidinthiones via
 Multicomponent Coupling of Terminal Alkynes, Elemental Sulfur, and
 Carbodiimides
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15108
_journal_page_last               15109
_journal_paper_doi               10.1021/ja9069419
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C15 H20 N2 S'
_chemical_formula_weight         260.39
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.589(2)
_cell_length_b                   14.928(3)
_cell_length_c                   15.567(3)
_cell_measurement_temperature    173(2)
_cell_volume                     2925.5(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_sigmaI/netI    0.0519
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14386
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.49
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  0.9598
_exptl_absorpt_correction_T_min  0.9311
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2591
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0379
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0200P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0661
_refine_ls_wR_factor_ref         0.0713
_reflns_number_gt                1607
_reflns_number_total             2591
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja9069419_si_001.cif
_cod_data_source_block           1a
_cod_original_cell_volume        2925.4(9)
_cod_database_code               4105207