Synthesis of 2,4,5-Trisubstituted Thiazoles via Lawesson's Reagent-Mediated Chemoselective Thionation-Cyclization of Functionalized Enamides
S. Vijay Kumar; G. Parameshwarappa; H. Ila; Journal of Organic Chemistry 78 (2013) 7362–7369; doi:10.1021/jo401208u

data_4028447
_publ_section_title
;
 Synthesis of 2,4,5-Trisubstituted Thiazoles via Lawesson's
 Reagent-Mediated Chemoselective Thionation-Cyclization of Functionalized
 Enamides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7362
_journal_page_last               7369
_journal_paper_doi               10.1021/jo401208u
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C20 H19 N O4 S'
_chemical_formula_weight         369.42
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 102.748(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            2
_cell_length_a                   8.526(5)
_cell_length_b                   7.988(5)
_cell_length_c                   13.822(5)
_cell_measurement_temperature    293(2)
_cell_volume                     918.2(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0505
_diffrn_reflns_av_sigmaI/netI    0.0517
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12564
_diffrn_reflns_theta_full        28.39
_diffrn_reflns_theta_max         28.39
_diffrn_reflns_theta_min         1.51
_exptl_absorpt_coefficient_mu    0.201
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_F_000             388
_refine_diff_density_max         0.099
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.024
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.00(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.814
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         3386
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.813
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0335
_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^)+(0.0460P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0780
_reflns_number_gt                2608
_reflns_number_total             3386
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401208u_si_002_1.cif
_cod_data_source_block           compound_1
_cod_database_code               4028447