A New Synthesis of 2,3-Dihydrobenzo[1,4]dioxine and 3,4-Dihydro-2H-benzo[1,4]oxazine Derivatives by Tandem Palladium-Catalyzed Oxidative Aminocarbonylation-Cyclization of 2-Prop-2-ynyloxyphenols and 2-Prop-2-ynyloxyanilines
Bartolo Gabriele; Giuseppe Salerno; Lucia Veltri; Raffaella Mancuso; Zhiyu Li; Alessandra Crispini; Anna Bellusci; Journal of Organic Chemistry 71 (2006) 7895–7898; doi:10.1021/jo061229l

data_4021987
_publ_contact_author_address
;
Dipartimento di Scienze Farmaceutiche
Universit\'a della Calabria
87030 Arcavacata di Rende (CS)
Italy
;
_publ_contact_author_email       b.gabriele@unical.it
_publ_contact_author_fax         0984492044
_publ_contact_author_name        'Gabriele, Bartolo'
_publ_contact_author_phone       0984492813
_publ_section_title
;
 A New Synthesis of 2,3-Dihydrobenzo[1,4]dioxine and
 3,4-Dihydro-2H-benzo[1,4]oxazine Derivatives by Tandem
 Palladium-Catalyzed Oxidative Aminocarbonylation-Cyclization
 of 2-Prop-2-ynyloxyphenols and 2-Prop-2-ynyloxyanilines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7895
_journal_page_last               7898
_journal_paper_doi               10.1021/jo061229l
_journal_volume                  71
_journal_year                    2006
_chemical_formula_moiety         'C14 H17 N2 O2'
_chemical_formula_sum            'C28 H34 N4 O4'
_chemical_formula_weight         490.59
_chemical_name_systematic
; 
(Z)-2-(4H-benzo[1,4]oxazin-3-ylidene)-N,N-diethylacetamide 
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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_method           SHELXL-97
_cell_angle_alpha                89.706(4)
_cell_angle_beta                 86.144(4)
_cell_angle_gamma                86.008(4)
_cell_formula_units_Z            2
_cell_length_a                   6.7277(4)
_cell_length_b                   13.3202(10)
_cell_length_c                   14.9976(11)
_cell_measurement_reflns_used    5480
_cell_measurement_temperature    298
_cell_measurement_theta_max      22.68
_cell_measurement_theta_min      3.07
_cell_volume                     1337.70(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21866
_diffrn_reflns_theta_full        24.71
_diffrn_reflns_theta_max         24.71
_diffrn_reflns_theta_min         1.36
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         4479
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0484
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0872P)^2^+0.3213P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1367
_refine_ls_wR_factor_ref         0.1643
_reflns_number_gt                3078
_reflns_number_total             4479
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo061229lsi20060614_013758.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
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_cod_database_code               4021987