Tf<sub>2</sub>O-Mediated Cyclization of α-Acyl-β-(2-aminopyridinyl)acrylamides: Access to N-Substituted 4<i>H</i>-Pyrido[1,2-<i>a</i>]pyrimidin-4-imines.
Bhujanga Rao, Chitturi; Zhang, Ning; Hu, Jiana; Wang, Yu; Liang, Yongjiu; Zhang, Rui; Yuan, Jingwen; Dong, Dewen; The Journal of organic chemistry 85 (2020) 4695–4705; doi:10.1021/acs.joc.9b03495

data_4038069
_publ_section_title
;
 Tf<sub>2</sub>O-Mediated Cyclization of
 \a-Acyl-\b-(2-aminopyridinyl)acrylamides: Access to N-Substituted
 4<i>H</i>-Pyrido[1,2-<i>a</i>]pyrimidin-4-imines.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4695
_journal_page_last               4705
_journal_paper_doi               10.1021/acs.joc.9b03495
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C18 H17 N3 O2'
_chemical_formula_sum            'C18 H17 N3 O2'
_chemical_formula_weight         307.35
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-05-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.2254(3)
_cell_length_b                   7.5242(2)
_cell_length_c                   30.3701(8)
_cell_measurement_reflns_used    9918
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      66.616
_cell_measurement_theta_min      3.341
_cell_volume                     3022.15(13)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      190.0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            28485
_diffrn_reflns_theta_full        66.69
_diffrn_reflns_theta_max         66.69
_diffrn_reflns_theta_min         2.91
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.730
_exptl_absorpt_correction_T_max  0.8678
_exptl_absorpt_correction_T_min  0.8163
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2660
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0372
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0532P)^2^+0.9128P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.0998
_reflns_number_gt                2455
_reflns_number_total             2660
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9b03495_si_002.cif
_cod_data_source_block           r
_cod_depositor_comments          'Adding full bibliography for 4038069.cif.'
_cod_database_code               4038069
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C13(H13), C16(H16), C15(H15), C14(H14), C5(H5), C3(H3)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C1(H1A,H1B,H1C), C18(H18A,H18B,H18C)
;
_olex2_submission_special_instructions 'No special instructions were received'