Regioselective Synthesis of N-Aminoisoindolones and Mono-N- and Di-N,N'-substituted Phthalazones Utilizing Hydrazine Nucleophiles in a Palladium-Catalyzed Three-Component Cascade Process
Ronald Grigg; Visuvanathar Sridharan; Mufakhrul Shah; Simon Mutton; Colin Kilner; David MacPherson; Peter Milner; Journal of Organic Chemistry 73 (2008) 8352–8356; doi:10.1021/jo800822p

data_4023786
_publ_contact_author_address
;
Department of Chemistry  
University of Leeds  
Leeds
LS2 9JT
UK
;
_publ_contact_author_email       R.Grigg@chemistry.leeds.ac.uk
_publ_contact_author_name        'Professor R.E.Grigg'
_publ_contact_author_phone       '+44 (0)113 34 36501'
_publ_section_title
;
 Regioselective Synthesis of N-Aminoisoindolones and Mono-N-
 and Di-N,N'-substituted Phthalazones Utilizing Hydrazine Nucleophiles
 in a Palladium-Catalyzed Three-Component Cascade Process
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8352
_journal_page_last               8356
_journal_paper_doi               10.1021/jo800822p
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C19 H18 N2 O4'
_chemical_formula_sum            'C19 H18 N2 O4'
_chemical_formula_weight         338.35
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.6420(2)
_cell_length_b                   8.3077(2)
_cell_length_c                   38.1238(8)
_cell_measurement_reflns_used    90546
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     3370.55(12)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1996)'
_computing_data_collection       'COLLECT (Nonius, 2004)'
_computing_data_reduction
;
DENZO-SMN and COLLECT (Otwinowski & Minor, 1996)
;
_computing_molecular_graphics
;
ORTEP-III Version 1.08 (Farrugia, 2005)
;
_computing_publication_material
;
enCIFer: A program for viewing, editing and visualising CIFs. 
F. H. Allen, O. Johnson, G. P. Shields, B. R. Smith, M. Towler, 
J. Applied Cryst., 37, 331-334, 2004
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
;
SIR92
Altomare, A.; Burla, M. C.; Camalli, G.; Cascarano, G.; 
Giacovazzo, C.; Guagliardi, A.; Polidori, G. 
J. Appl. Cryst. 1994, 27, 435-436. 
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
;
Nonius KappaCCD area-detector diffractometer
;
_diffrn_measurement_method
;       
phi and omega scans to fill the asymmetric unit
;
_diffrn_radiation_detector       'CCD plate'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2175
_diffrn_reflns_av_sigmaI/netI    0.0933
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            22230
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.87
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.73
_exptl_crystal_size_mid          0.65
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.119
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3310
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.1283
_refine_ls_R_factor_gt           0.0872
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1481P)^2^+0.2657P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2063
_refine_ls_wR_factor_ref         0.2456
_reflns_number_gt                2094
_reflns_number_total             3310
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800822p_si_004.cif
_cod_data_source_block           ms407
_cod_database_code               4023786