Microwave-assisted domino and multicomponent reactions with cyclic acylketenes: expeditious syntheses of oxazinones and oxazindiones.
Presset, Marc; Coquerel, Yoann; Rodriguez, Jean; Organic letters 11 (2009) 5706–5709; doi:10.1021/ol9024056

data_1504304
_publ_section_title
;
 Microwave-assisted domino and multicomponent reactions with cyclic
 acylketenes: expeditious syntheses of oxazinones and oxazindiones.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              5706
_journal_page_last               5709
_journal_paper_doi               10.1021/ol9024056
_journal_volume                  11
_journal_year                    2009
_chemical_absolute_configuration unk
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C16 H19 N1 O3'
_chemical_formula_sum            'C16 H19 N O3'
_chemical_formula_weight         273.32
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2009-07-10T17:06:21-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2054(1)
_cell_length_b                   10.3040(2)
_cell_length_c                   21.8082(6)
_cell_measurement_reflns_used    12742
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.68
_cell_measurement_theta_min      1.87
_cell_measurement_wavelength     0.71073
_cell_volume                     1394.43(5)
_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-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Omega + Phi scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.053
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            12742
_diffrn_reflns_theta_full        28.68
_diffrn_reflns_theta_max         28.68
_diffrn_reflns_theta_min         1.87
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.09
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.147
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.7(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.189
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         1989
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.189
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0895P)^2^+0.1161P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1497
_reflns_number_gt                1654
_reflns_number_total             1989
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol9024056_si_002.cif
_cod_data_source_block           map04180
_cod_database_code               1504304