Tandem Reactions of 1,3-Diacid Chlorides with 2-Methylimidazoline and 2-Methyl-1,4,5,6-tetrahydropyrimidine: One-Pot Synthesis of 1,8-Naphthyridinetetraones
Guozhong Ye; Aihua Zhou; William P. Henry; Yingquan Song; Sabornie Chatterjee; Debbie J. Beard; Pittman, Jr., Charles U.; Journal of Organic Chemistry 73 (2008) 5170–5172; doi:10.1021/jo8009177

data_4023524
_publ_contact_author_address
;Department of Chemistry
Mississippi State University
Box 9573
Mississippi State, MS   39762
;
_publ_contact_author_email       cpittman@chemistry.msstate.edu
_publ_contact_author_fax         1(662)3251618
_publ_contact_author_name        'Charles U. Pittman, Jr.'
_publ_contact_author_phone       1(662)3257616
_publ_section_title
;
 Tandem Reactions of 1,3-Diacid Chlorides with 2-Methylimidazoline
 and 2-Methyl-1,4,5,6-tetrahydropyrimidine:
 One-Pot Synthesis of 1,8-Naphthyridinetetraones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5170
_journal_page_last               5172
_journal_paper_doi               10.1021/jo8009177
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C22 H32 N2 O4'
_chemical_formula_weight         388.50
_chemical_name_systematic
;
5,5,8,8-Tetra-n-butyl-1,2-dihydroimidazo[1,2,3-ij][1,8]naphthyridine-
4,6,7,9(5H,8H)tetraone
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.008(15)
_cell_angle_beta                 90.126(16)
_cell_angle_gamma                104.101(15)
_cell_formula_units_Z            5
_cell_length_a                   10.815(9)
_cell_length_b                   11.663(10)
_cell_length_c                   21.724(18)
_cell_measurement_temperature    273(2)
_cell_volume                     2658(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.3287
_diffrn_reflns_av_sigmaI/netI    0.2807
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            20074
_diffrn_reflns_theta_full        25.26
_diffrn_reflns_theta_max         25.26
_diffrn_reflns_theta_min         1.80
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.083
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cubic
_exptl_crystal_F_000             1050
_exptl_crystal_size_max          0.73
_exptl_crystal_size_mid          0.66
_exptl_crystal_size_min          0.57
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0005(15)
_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   0.878
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     604
_refine_ls_number_reflns         9417
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.878
_refine_ls_R_factor_all          0.1651
_refine_ls_R_factor_gt           0.0892
_refine_ls_shift/su_max          0.262
_refine_ls_shift/su_mean         0.020
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0153P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2202
_refine_ls_wR_factor_ref         0.2706
_reflns_number_gt                3852
_reflns_number_total             9417
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8009177-File001.cif
_cod_data_source_block           wph052m
_cod_database_code               4023524