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_4105646
_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            'C27 H22 N2 O4'
_chemical_formula_weight         438.47
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                112.395(2)
_cell_angle_beta                 97.263(2)
_cell_angle_gamma                111.677(2)
_cell_formula_units_Z            2
_cell_length_a                   10.2580(17)
_cell_length_b                   10.8760(18)
_cell_length_c                   12.051(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1097.9(3)
_computing_cell_refinement       'SMART (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1998)'
_computing_publication_material  'SHELXTL (Bruker, 1998)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.902
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0684
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6755
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.21
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9875
_exptl_absorpt_correction_T_min  0.9814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4883
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1246
_refine_ls_R_factor_gt           0.0553
_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^)+(0.0668P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1250
_refine_ls_wR_factor_ref         0.1532
_reflns_number_gt                2556
_reflns_number_total             4883
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja110870f_si_002.cif
_cod_data_source_block           11
_cod_database_code               4105646