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_4028448
_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            'C22 H14 F2 N2 O S'
_chemical_formula_weight         392.41
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.7790(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1709(2)
_cell_length_b                   10.0287(3)
_cell_length_c                   29.5929(7)
_cell_measurement_temperature    295(2)
_cell_volume                     1825.02(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0541
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            30820
_diffrn_reflns_theta_full        29.55
_diffrn_reflns_theta_max         29.55
_diffrn_reflns_theta_min         1.38
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_T_max  0.9895
_exptl_absorpt_correction_T_min  0.9750
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         5109
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0435
_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^)+(0.0817P)^2^+0.1047P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1231
_refine_ls_wR_factor_ref         0.1533
_reflns_number_gt                3426
_reflns_number_total             5109
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo401208u_si_002_2.cif
_cod_data_source_block           compound_2
_cod_database_code               4028448