Four-Component Cascade Heteroannulation of Heterocyclic Ketene Aminals: Synthesis of Functionalized Tetrahydroimidazo[1,2-a]pyridine Derivatives
Ming Li; Peng Shao; Shu-Wen Wang; Wei Kong; Li-Rong Wen; Journal of Organic Chemistry 77 (2012) 8956–8967; doi:10.1021/jo3013836

data_4027583
_publ_section_title
;
 Four-Component Cascade Heteroannulation of Heterocyclic Ketene Aminals:
 Synthesis of Functionalized Tetrahydroimidazo[1,2-a]pyridine Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8956
_journal_page_last               8967
_journal_paper_doi               10.1021/jo3013836
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C28 H22 Cl3 N3 O2'
_chemical_formula_sum            'C28 H22 Cl3 N3 O2'
_chemical_formula_weight         538.84
_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                 99.091(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.495(4)
_cell_length_b                   11.278(3)
_cell_length_c                   18.337(5)
_cell_measurement_reflns_used    7588
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      1.65
_cell_volume                     2551.6(13)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELX97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0949
_diffrn_reflns_av_sigmaI/netI    0.0949
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15554
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    0.391
_exptl_absorpt_correction_T_max  0.9620
_exptl_absorpt_correction_T_min  0.9437
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_description       plate
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.286
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4492
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.286
_refine_ls_R_factor_all          0.1439
_refine_ls_R_factor_gt           0.1141
_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^)+(0.0065P)^2^+5.5859P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1456
_refine_ls_wR_factor_ref         0.1550
_reflns_number_gt                3574
_reflns_number_total             4492
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3013836_si_002.cif
_cod_data_source_block           mx1406
_cod_original_cell_volume        2551.6(12)
_cod_database_code               4027583