Cyclization and N-Iodosuccinimide-Induced Electrophilic Iodocyclization of 3-Aza-1,5-enynes To Synthesize 1,2-Dihydropyridines and 3-Iodo-1,2-dihydropyridines
Xiaoyi Xin; Dongping Wang; Fan Wu; Xincheng Li; Boshun Wan; Journal of Organic Chemistry 78 (2013) 4065–4074; doi:10.1021/jo400387b

data_4028177
_publ_section_title
;
 Cyclization and N-Iodosuccinimide-Induced Electrophilic Iodocyclization
 of 3-Aza-1,5-enynes To Synthesize 1,2-Dihydropyridines and
 3-Iodo-1,2-dihydropyridines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4065
_journal_page_last               4074
_journal_paper_doi               10.1021/jo400387b
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C28 H25 N O6 S'
_chemical_formula_weight         503.55
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 93.348(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.4116(4)
_cell_length_b                   9.9944(3)
_cell_length_c                   19.1950(6)
_cell_measurement_reflns_used    5070
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.67
_cell_measurement_theta_min      2.30
_cell_volume                     2568.52(14)
_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  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14412
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.855
_refine_diff_density_min         -0.664
_refine_diff_density_rms         0.131
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4510
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0768
_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^)+(0.1510P)^2^+0.7541P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2145
_refine_ls_wR_factor_ref         0.2297
_reflns_number_gt                3448
_reflns_number_total             4510
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400387b_si_001.cif
_cod_data_source_block           2
_cod_database_code               4028177