Regioselective Synthesis of 2,4,5-Trisubstituted Oxazoles and Ketene Aminals via Hydroamidation and Iodo-Imidation of Ynamides.
Mallick, Rajendra K.; Prabagar, B.; Sahoo, Akhila K.; The Journal of organic chemistry 82 (2017) 10583–10594; doi:10.1021/acs.joc.7b02124

data_4032892
_publ_section_title
;
 Regioselective Synthesis of 2,4,5-Trisubstituted Oxazoles and Ketene
 Aminals via Hydroamidation and Iodo-Imidation of Ynamides.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10583
_journal_page_last               10594
_journal_paper_doi               10.1021/acs.joc.7b02124
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C26 H21 I N2 O4 S'
_chemical_formula_weight         584.41
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 109.063(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   32.959(4)
_cell_length_b                   8.5274(8)
_cell_length_c                   18.548(2)
_cell_measurement_reflns_used    9780
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.38
_cell_measurement_theta_min      2.26
_cell_volume                     4927.1(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0595
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
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_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            82281
_diffrn_reflns_theta_full        28.43
_diffrn_reflns_theta_max         28.43
_diffrn_reflns_theta_min         2.26
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_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.8858
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2336
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.745
_refine_diff_density_min         -1.024
_refine_diff_density_rms         0.138
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         6182
_refine_ls_number_restraints     0
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_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0370
_refine_ls_shift/su_max          0.01
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0476P)^2^+2.9444P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0942
_reflns_number_gt                4535
_reflns_number_total             6182
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b02124_si_002.cif
_cod_data_source_block           bala_compound_4a
_cod_depositor_comments
'Adding full bibliography for 4032890--4032892.cif.'
_cod_original_cell_volume        4927.0(9)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4032892