FeCl3-Catalyzed Cascade Cyclization in One Pot: Synthesis of Ring-Fused Tetrahydroquinoline Derivatives from Arylamines and N-Substituted Lactams
Manman Sun; Tianshui Zhang; Weiliang Bao; Journal of Organic Chemistry 78 (2013) 8155–8160; doi:10.1021/jo400979h

data_4028493
_publ_section_title
;
 FeCl3-Catalyzed Cascade Cyclization in One Pot: Synthesis of Ring-Fused
 Tetrahydroquinoline Derivatives from Arylamines and N-Substituted Lactams
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8155
_journal_page_last               8160
_journal_paper_doi               10.1021/jo400979h
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C13 H17 N3 O'
_chemical_formula_sum            'C13 H17 N3 O'
_chemical_formula_weight         231.30
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P -2ac -2n'
_symmetry_space_group_name_H-M   'P n 21 a'
_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            8
_cell_length_a                   20.1281(17)
_cell_length_b                   14.9938(16)
_cell_length_c                   8.0453(7)
_cell_measurement_reflns_used    1774
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3977
_cell_measurement_theta_min      2.8675
_cell_volume                     2428.0(4)
_computing_cell_refinement       'CrysAlis PRO (Agilent Technologies, 2011)'
_computing_data_collection       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  OLEX2
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w 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  0.0447
_diffrn_reflns_av_sigmaI/netI    0.0433
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9664
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.87
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9836
_exptl_absorpt_correction_T_min  0.9613
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis PRO (Agilent Technologies, 2011) 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.688
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.093
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         3426
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.1181
_refine_ls_R_factor_gt           0.0928
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1647P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2086
_refine_ls_wR_factor_ref         0.2376
_reflns_number_gt                2485
_reflns_number_total             3426
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400979h_si_001.cif
_cod_data_source_block           121108_smm01
_cod_database_code               4028493