Brønsted Acid Catalyzed and NIS-Promoted Cyclization of Diynones: Selective Synthesis of 4-Pyrone, 4-Pyridone, and 3-Pyrrolone Derivatives
Yi-Feng Qiu; Fang Yang; Zi-Hang Qiu; Mei-Jin Zhong; Li-Jing Wang; Yu-Ying Ye; Bo Song; Yong-Min Liang; Journal of Organic Chemistry 78 (2013) 12018–12028; doi:10.1021/jo402055a

data_4028825
_publ_contact_author_name
;
;
_publ_section_title
;
 Br\/onsted Acid Catalyzed and NIS-Promoted Cyclization of Diynones:
 Selective Synthesis of 4-Pyrone, 4-Pyridone, and 3-Pyrrolone Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              12018
_journal_page_last               12028
_journal_paper_doi               10.1021/jo402055a
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C24 H19 N O'
_chemical_formula_sum            'C24 H19 N O'
_chemical_formula_weight         337.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_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     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-10-15
_audit_creation_method
;
  Olex2 1.2
  (compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 102.041(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            12
_cell_length_a                   19.701(3)
_cell_length_b                   10.1591(12)
_cell_length_c                   29.095(5)
_cell_measurement_reflns_used    2058
_cell_measurement_temperature    292.53(10)
_cell_measurement_theta_max      28.5791
_cell_measurement_theta_min      3.0963
_cell_volume                     5695.1(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      292.53(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9711
_diffrn_measured_fraction_theta_max 0.9668
_diffrn_measurement_details
;
  1 omega  -83.00  -58.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3492  178.0000  120.0000 25

  2 omega   -4.00   23.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3492  -99.0000 -150.0000 27

  3 omega   -7.00   64.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305   77.0000  -30.0000 71

  4 omega    8.00   60.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305  -87.0000  134.0000 52

  5 omega   17.00   45.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305  -99.0000  120.0000 28

  6 omega   11.00   88.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305   38.0000   90.0000 77
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0018243000
_diffrn_orient_matrix_UB_12      0.0665337000
_diffrn_orient_matrix_UB_13      -0.0076004000
_diffrn_orient_matrix_UB_21      -0.0321805000
_diffrn_orient_matrix_UB_22      -0.0131536000
_diffrn_orient_matrix_UB_23      -0.0153751000
_diffrn_orient_matrix_UB_31      -0.0177142000
_diffrn_orient_matrix_UB_32      0.0169453000
_diffrn_orient_matrix_UB_33      0.0180594000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_av_unetI/netI     0.0814
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            24283
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         3.10
_diffrn_source                   'SuperNova (Mo) x-ray Source'
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63487
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_description       block
_exptl_crystal_F_000             2136
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.926
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     704
_refine_ls_number_reflns         10515
_refine_ls_number_restraints     216
_refine_ls_restrained_S_all      0.941
_refine_ls_R_factor_all          0.2162
_refine_ls_R_factor_gt           0.0604
_refine_ls_shift/su_max          0.054
_refine_ls_shift/su_mean         0.013
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0777P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1548
_refine_ls_wR_factor_ref         0.2570
_reflns_number_gt                2305
_reflns_number_total             10515
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo402055a_si_002.cif
_cod_data_source_block           qiuyf1011
_cod_original_cell_volume        5694.9(14)
_cod_database_code               4028825
_reflns_odcompleteness_completeness 97.11
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32