SnCl2-Catalyzed Selective Atom Economic Imino Diels-Alder Reaction: Synthesis of 2-(1H-Pyrrolo[2,3-b]pyridin-3-yl)quinolines
Rajendran Suresh; Shanmugam Muthusubramanian; Rajendran Senthilkumaran; Govindaswamy Manickam; Journal of Organic Chemistry 77 (2012) 1468–1476; doi:10.1021/jo202256z

data_4026924
_publ_contact_author_address
;
Department of Organic Chemistry
School of Chemistry
Madurai Kamaraj University
Madurai 625 021
India
;
_publ_contact_author_email       muthumanian2001@yahoo.com
_publ_contact_author_name        'Prof.Shanmugam Muthusubramanian'
_publ_contact_author_phone       '0452 2458246'
_publ_section_title
;
 SnCl2-Catalyzed Selective Atom Economic Imino Diels-Alder Reaction:
 Synthesis of 2-(1H-Pyrrolo[2,3-b]pyridin-3-yl)quinolines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1468
_journal_page_last               1476
_journal_paper_doi               10.1021/jo202256z
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C29 H21 N3 O3 S'
_chemical_formula_weight         491.55
_chemical_melting_point          508(1)
_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_date             '27 August 2011'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                72.212(2)
_cell_angle_beta                 81.277(2)
_cell_angle_gamma                83.828(2)
_cell_formula_units_Z            2
_cell_length_a                   8.2737(3)
_cell_length_b                   11.8237(4)
_cell_length_c                   12.6735(4)
_cell_measurement_reflns_used    5739
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.02
_cell_measurement_theta_min      2.49
_cell_volume                     1164.40(7)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       '\w and \f scan'
_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  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            30765
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         31.88
_diffrn_reflns_theta_min         1.81
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_T_max  0.9569
_exptl_absorpt_correction_T_min  0.8804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         7891
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0465
_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^)+(0.0844P)^2^+0.1238P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1496
_reflns_number_gt                5762
_reflns_number_total             7891
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202256z_si_001.cif
_cod_data_source_block           hda
_cod_database_code               4026924