From nitrobenzenes to substituted tetrahydroquinolines in a single step by a domino reduction/imine formation/aza-diels-alder reaction.
Imrich, Hans-Georg; Conrad, Jürgen; Bubrin, Denis; Beifuss, Uwe; The Journal of organic chemistry 80 (2015) 2319–2332; doi:10.1021/jo502882y

data_4030674
_publ_section_title
;
 From nitrobenzenes to substituted tetrahydroquinolines in a single step
 by a domino reduction/imine formation/aza-diels-alder reaction.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2319
_journal_page_last               2332
_journal_paper_doi               10.1021/jo502882y
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C18 H16 Br N'
_chemical_formula_sum            'C18 H16 Br N'
_chemical_formula_weight         326.23
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_symmetry_space_group_name_Hall  '-P 1'
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_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                102.428(15)
_cell_angle_beta                 108.884(14)
_cell_angle_gamma                114.342(14)
_cell_formula_units_Z            2
_cell_length_a                   9.2639(17)
_cell_length_b                   9.809(2)
_cell_length_c                   10.047(2)
_cell_measurement_reflns_used    61
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      12.5
_cell_measurement_theta_min      6
_cell_volume                     719.8(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_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  0.2269
_diffrn_reflns_av_sigmaI/netI    0.0851
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3016
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    2.844
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.885
_refine_diff_density_min         -1.722
_refine_diff_density_rms         0.149
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2728
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0581
_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^)+(0.0865P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1360
_refine_ls_wR_factor_ref         0.1457
_reflns_number_gt                1941
_reflns_number_total             2728
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo502882y_si_002.cif
_cod_data_source_block           i01
_cod_depositor_comments
'Adding full bibliography for 4030673--4030675.cif.'
_cod_original_cell_volume        719.9(3)
_cod_database_code               4030674