Copper-Catalyzed Tandem Synthesis of Indolo-, Pyrrolo[2,1-a]isoquinolines, Naphthyridines and Bisindolo/Pyrrolo[2,1-a]isoquinolines via Hydroamination of ortho-Haloarylalkynes Followed by C-2 Arylation
Akhilesh K. Verma; Rajeev R. Jha; Ritu Chaudhary; Rakesh K. Tiwari; Kotla Siva K. Reddy; Abhinandan Danodia; Journal of Organic Chemistry 77 (2012) 8191–8205; doi:10.1021/jo301572p

data_4027524
_publ_contact_author_address
;
 1711 Gilman Hall, Iowa State University,
 Ames, Iowa, 50011, USA
;
_publ_contact_author_email       ellern@iastate.edu
_publ_contact_author_fax         +1-515-2945717
_publ_contact_author_name        'Dr. Arkady M. Ellern'
_publ_contact_author_phone       +1-515-2947956
_publ_section_title
;
 Copper-Catalyzed Tandem Synthesis of Indolo-,
 Pyrrolo[2,1-a]isoquinolines, Naphthyridines and
 Bisindolo/Pyrrolo[2,1-a]isoquinolines via Hydroamination of
 ortho-Haloarylalkynes Followed by C-2 Arylation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8191
_journal_page_last               8205
_journal_paper_doi               10.1021/jo301572p
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C24 H17 N'
_chemical_formula_weight         319.39
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'APEX2 v2009.11-0'
_cell_angle_alpha                90
_cell_angle_beta                 90.225(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6169(5)
_cell_length_b                   12.7831(9)
_cell_length_c                   13.5263(9)
_cell_measurement_reflns_used    6149
_cell_measurement_temperature    173.(2)
_cell_measurement_theta_max      28.2177
_cell_measurement_theta_min      2.1916
_cell_volume                     1662.83(18)
_computing_cell_refinement       'SAINT V7.66A (Bruker AXS, 2009)'
_computing_data_collection       'APEX2 Suite (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.66A (Bruker AXS, 2009)'
_computing_molecular_graphics    'XSHELL (Bruker AXS, 2007)'
_computing_publication_material  'APEX2 Suite (Bruker AXS, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  ' BRUKER APEX2 CCD Diffractometer'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19131
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.339
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4130
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0527
_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^)+(0.0628P)^2^+0.9302P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1429
_reflns_number_gt                3352
_reflns_number_total             4130
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301572p_si_001.cif
_cod_data_source_block           I
_cod_original_cell_volume        1662.8(2)
_cod_database_code               4027524