A practical two-step synthesis of imidazo[1,2-a]pyridines from N-(prop-2-yn-1-yl)pyridin-2-amines.
Sucunza, David; Samadi, Abdelouahid; Chioua, Mourad; Silva, Daniel B.; Yunta, Cristina; Infantes, Lourdes; Carmo Carreiras, M.; Soriano, Elena; Marco-Contelles, José; Chemical communications (Cambridge, England) 47 (2011) 5043–5045; doi:10.1039/c1cc10641d

data_7112704
_publ_section_title
;
 A practical two-step synthesis of imidazo[1,2-a]pyridines from
 N-(prop-2-yn-1-yl)pyridin-2-amines.
;
_journal_issue                   17
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5043
_journal_page_last               5045
_journal_paper_doi               10.1039/c1cc10641d
_journal_volume                  47
_journal_year                    2011
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C11 H7 Cl1 N4 O1'
_chemical_formula_sum            'C11 H7 Cl N4 O'
_chemical_formula_weight         246.66
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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_date             2010-07-22T18:35:54-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                82.408(2)
_cell_angle_beta                 81.742(2)
_cell_angle_gamma                82.153(2)
_cell_formula_units_Z            2
_cell_length_a                   5.9010(4)
_cell_length_b                   8.9910(7)
_cell_length_c                   10.1390(8)
_cell_measurement_reflns_used    4784
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      64.89
_cell_measurement_theta_min      4.44
_cell_volume                     523.89(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.927
_diffrn_measured_fraction_theta_max 0.927
_diffrn_radiation_monochromator  'Mirrors, multilayer'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5676
_diffrn_reflns_theta_full        65.97
_diffrn_reflns_theta_max         65.97
_diffrn_reflns_theta_min         4.44
_exptl_absorpt_coefficient_mu    3.142
_exptl_absorpt_correction_T_max  0.7527
_exptl_absorpt_correction_T_min  0.5440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2008
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.125
_refine_ls_extinction_coef       0.020(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   0.734
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         1683
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.734
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0458
_refine_ls_shift/su_max          0.043
_refine_ls_shift/su_mean         0.008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1281P)^2^+0.7995P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1308
_reflns_number_gt                1543
_reflns_number_total             1683
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc10641d.txt
_cod_data_source_block           dsb48
_cod_original_formula_sum        'C11 H7 Cl1 N4 O1'
_cod_database_code               7112704