CuCN-Mediated Cascade Cyclization of 4-(2-Bromophenyl)-2-butenoates: A High-Yield Synthesis of Substituted Naphthalene Amino Esters
R. Santhosh Reddy; Pragati K Prasad; Brij Bhushan Ahuja; Arumugam Sudalai; Journal of Organic Chemistry 78 (2013) 5045–5050; doi:10.1021/jo400244h

data_4028222
_publ_contact_author
;

Dr. A. Sudalai

Scientist
CEPD  
National Chemical Laboratory
Dr. Homi Bhaba Road
Pune 411008, India
;
_publ_contact_author_email       a.sudalai@ncl.res.in
_publ_contact_author_fax         '91 020 2590 2547'
_publ_contact_author_phone       '91 020 2590 2174'
_publ_section_title
;
 CuCN-Mediated Cascade Cyclization of 4-(2-Bromophenyl)-2-butenoates: A
 High-Yield Synthesis of Substituted Naphthalene Amino Esters
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5045
_journal_page_last               5050
_journal_paper_doi               10.1021/jo400244h
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C14 H12 N O4'
_chemical_formula_sum            'C14 H12 N O4'
_chemical_formula_weight         258.25
_chemical_name_systematic
; 
 ? 
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 99.538(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1713(4)
_cell_length_b                   11.2608(8)
_cell_length_c                   15.5138(9)
_cell_measurement_reflns_used    3394
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.360
_cell_volume                     1235.49(13)
_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 0.970
_diffrn_measured_fraction_theta_max 0.970
_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  0.0203
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            3394
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         2.97
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.8787
_exptl_absorpt_correction_T_min  0.7076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, Acta Cryst. (1995) A51 33-58'
_exptl_crystal_colour            PINK
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       rod
_exptl_crystal_F_000             540.30
_exptl_crystal_size_max          0.552
_exptl_crystal_size_mid          0.332
_exptl_crystal_size_min          0.241
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.434
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3394
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.434
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0680
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2185
_refine_ls_wR_factor_ref         0.2476
_reflns_number_gt                1911
_reflns_number_total             3394
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400244h.cif
_cod_data_source_block           NO2NaptCOOH
_cod_original_cell_volume        1235.49(14)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4028222