Facile synthesis of 2,5-disubstituted thiazoles from terminal alkynes, sulfonyl azides, and thionoesters.
Miura, Tomoya; Funakoshi, Yuuta; Fujimoto, Yoshikazu; Nakahashi, Junki; Murakami, Masahiro; Organic letters 17 (2015) 2454–2457; doi:10.1021/acs.orglett.5b00960

data_1520754
_publ_section_title
;
 Facile synthesis of 2,5-disubstituted thiazoles from terminal alkynes,
 sulfonyl azides, and thionoesters.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2454
_journal_page_last               2457
_journal_paper_doi               10.1021/acs.orglett.5b00960
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C23 H21 N O3 S2'
_chemical_formula_weight         423.53
_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                88.1161(18)
_cell_angle_beta                 89.150(2)
_cell_angle_gamma                62.1966(18)
_cell_formula_units_Z            2
_cell_length_a                   7.6670(6)
_cell_length_b                   8.7269(6)
_cell_length_c                   17.0497(13)
_cell_measurement_temperature    108(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.00
_cell_volume                     1008.54(13)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        'Yadokari-XG (Wakita, 2000)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, 2000)'
_computing_publication_material  'Yadokari-XG (Wakita, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      108(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_sigmaI/netI    0.0676
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9691
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    0.289
_exptl_absorpt_correction_T_max  0.8931
_exptl_absorpt_correction_T_min  0.8931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.620
_refine_diff_density_min         -0.859
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4570
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0681
_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^)+(0.0875P)^2^+1.1691P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1743
_refine_ls_wR_factor_ref         0.1959
_reflns_number_gt                3290
_reflns_number_total             4570
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol5b00960_si_001.cif
_cod_data_source_block           1
_cod_original_sg_symbol_Hall     -p_1
_cod_original_sg_symbol_H-M      p_-1
_cod_database_code               1520754