The regioselective synthesis of spirooxindolo pyrrolidines and pyrrolizidines via three-component reactions of acrylamides and aroylacrylic acids with isatins and α-amino acids.
Pavlovskaya, Tatyana L.; Yaremenko, Fedor G.; Lipson, Victoria V.; Shishkina, Svetlana V.; Shishkin, Oleg V.; Musatov, Vladimir I.; Karpenko, Alexander S.; Beilstein journal of organic chemistry 10 (2014) 117–126; doi:10.3762/bjoc.10.8

data_4028968
_publ_section_title
;
 The regioselective synthesis of spirooxindolo pyrrolidines and
 pyrrolizidines via three-component reactions of acrylamides and
 aroylacrylic acids with isatins and \a-amino acids.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              117
_journal_page_last               126
_journal_paper_doi               10.3762/bjoc.10.8
_journal_volume                  10
_journal_year                    2014
_chemical_formula_moiety         'C13 H14 Br N3 O2'
_chemical_formula_sum            'C13 H14 Br N3 O2'
_chemical_formula_weight         324.18
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.994(4)
_cell_angle_beta                 90.947(4)
_cell_angle_gamma                106.218(5)
_cell_formula_units_Z            2
_cell_length_a                   6.9659(3)
_cell_length_b                   7.5441(4)
_cell_length_c                   13.4092(5)
_cell_measurement_reflns_used    1901
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      31.9
_cell_measurement_theta_min      3.0
_cell_volume                     676.36(6)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET)
(compiled Apr  1 2005,17:53:34)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET)
(compiled Apr  1 2005,17:53:34)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET)
(compiled Apr  1 2005,17:53:34)
;
_computing_molecular_graphics    'XP (Siemens, 1998)'
_computing_publication_material  'SHELXTL (Sheldrick, 1998)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 1998)'
_computing_structure_solution    'SHELXTL (Sheldrick, 1998)'
_diffrn_ambient_temperature      273(2)
_diffrn_detector_area_resol_mean 16.1827
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  Xcalibur"3
_diffrn_measurement_method       \w-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6331
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         3.04
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    3.040
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5815
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       stick
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.041
_refine_diff_density_min         -1.005
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3908
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0464
_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^)+(0.0404P)^2^+0.4820P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1110
_reflns_number_gt                2795
_reflns_number_total             3908
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1860-5397-10-8-S3.cif
_cod_data_source_block           4a
_cod_original_cell_volume        676.36(5)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4028968