Aza-Oxy-Carbanion Relay via Non-Brook Rearrangement: Efficient Synthesis of Furo[3,2-c]pyridinones
Fushun Liang; Shaoxia Lin; Ying Wei; Journal of the American Chemical Society 133 (2011) 1781–1783; doi:10.1021/ja110870f

data_4105647
_publ_section_title
;
 Aza-Oxy-Carbanion Relay via Non-Brook Rearrangement: Efficient Synthesis
 of Furo[3,2-c]pyridinones
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1781
_journal_page_last               1783
_journal_paper_doi               10.1021/ja110870f
_journal_volume                  133
_journal_year                    2011
_chemical_formula_sum            'C29 H25 N O2'
_chemical_formula_weight         419.50
_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                90.00
_cell_angle_beta                 101.770(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.619(2)
_cell_length_b                   11.3289(16)
_cell_length_c                   15.146(3)
_cell_measurement_temperature    293(2)
_cell_volume                     2287.7(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0692
_diffrn_reflns_av_sigmaI/netI    0.2722
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8616
_diffrn_reflns_theta_full        24.71
_diffrn_reflns_theta_max         24.71
_diffrn_reflns_theta_min         3.06
_exptl_absorpt_coefficient_mu    0.076
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_F_000             888
_refine_diff_density_max         0.115
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.025
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.591
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3865
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.591
_refine_ls_R_factor_all          0.1826
_refine_ls_R_factor_gt           0.0374
_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^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0389
_refine_ls_wR_factor_ref         0.0467
_reflns_number_gt                1058
_reflns_number_total             3865
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja110870f_si_003.cif
_cod_data_source_block           exp_6878
_cod_original_cell_volume        2287.7(6)
_cod_database_code               4105647