Chemoselective Azidation of o-Alkynylaldehydes over [3 + 2] Cycloaddition and Subsequent Staudinger Reaction: Access to Benzonaphthyridines/Naphthyridines.
Kumar, Pradeep; Aggarwal, Trapti; Verma, Akhilesh K.; The Journal of organic chemistry 82 (2017) 6388–6397; doi:10.1021/acs.joc.7b01016

data_4032559
_publ_section_title
;
 Chemoselective Azidation of o-Alkynylaldehydes over [3 + 2] Cycloaddition
 and Subsequent Staudinger Reaction: Access to
 Benzonaphthyridines/Naphthyridines.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6388
_journal_page_last               6397
_journal_paper_doi               10.1021/acs.joc.7b01016
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C19 H14 N4 O'
_chemical_formula_sum            'C19 H14 N4 O'
_chemical_formula_weight         314.34
_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           SHELXL-97
_cell_angle_alpha                90.000(12)
_cell_angle_beta                 92.26
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.3912(6)
_cell_length_b                   5.576(3)
_cell_length_c                   18.214
_cell_measurement_reflns_used    718
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      19.2350
_cell_measurement_theta_min      3.6390
_cell_volume                     1561.9(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'xcalibur sapphire3'
_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  0.0766
_diffrn_reflns_av_sigmaI/netI    0.1360
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9740
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.40
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9829
_exptl_absorpt_correction_T_min  0.9795
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.916
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2762
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.916
_refine_ls_R_factor_all          0.2081
_refine_ls_R_factor_gt           0.0774
_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^)+(0.0557P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1377
_refine_ls_wR_factor_ref         0.1911
_reflns_number_gt                1113
_reflns_number_total             2762
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b01016_si_002.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 4032559.cif.'
_cod_original_cell_volume        1561.8(8)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4032559