Au(I)-Catalyzed Cascade Reaction Involving Formal Double Hydroamination of Alkynes Bearing Tethered Carboxylic Groups: An Easy Access to Fused Dihydrobenzimidazoles and Tetrahydroquinazolines
Nitin T. Patil; Anil Kumar Mutyala; Pediredla G. V. V. Lakshmi; Balakrishna Gajula; Balasubramanian Sridhar; Gurava Reddy Pottireddygari; Tadikamalla Prabhakar Rao; Journal of Organic Chemistry 75 (2010) 5963–5975; doi:10.1021/jo1013228

data_4025658
_publ_section_title
;
 Au(I)-Catalyzed Cascade Reaction Involving Formal Double Hydroamination
 of Alkynes Bearing Tethered Carboxylic Groups: An Easy Access to Fused
 Dihydrobenzimidazoles and Tetrahydroquinazolines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5963
_journal_page_last               5975
_journal_paper_doi               10.1021/jo1013228
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C22 H26 N2 O'
_chemical_formula_sum            'C22 H26 N2 O'
_chemical_formula_weight         334.45
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5601(6)
_cell_length_b                   13.1228(7)
_cell_length_c                   13.8186(8)
_cell_measurement_reflns_used    7647
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      22.69
_cell_measurement_theta_min      5.44
_cell_volume                     1914.96(19)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       '\w scan'
_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  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0125
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18515
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.14
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.160
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.026
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         1934
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0407
_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^)+(0.0656P)^2^+0.3725P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1206
_reflns_number_gt                1771
_reflns_number_total             1934
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo1013228_si_001_1.cif
_cod_data_source_block           ah56m
_cod_original_cell_volume        1914.95(19)
_cod_database_code               4025658