Oxidative annulation of L-phenylalanine using I<sub>2</sub>/DMSO: an easy approach for chemoselective synthesis of 2,3,5-trisubstituted pyridines and 2,5-disubstituted oxazoles.
Devaraju, Mohankumar; Prasad Dasappa, Jagadeesh; Organic & biomolecular chemistry 23 (2025) 3437–3442; doi:10.1039/d5ob00039d

data_7160413
_publ_section_title
;
 Oxidative annulation of L-phenylalanine using I<sub>2</sub>/DMSO: an easy
 approach for chemoselective synthesis of 2,3,5-trisubstituted pyridines
 and 2,5-disubstituted oxazoles.
;
_journal_issue                   14
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3437
_journal_page_last               3442
_journal_paper_doi               10.1039/d5ob00039d
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         C18H15NO4
_chemical_formula_sum            'C18 H15 N O4'
_chemical_formula_weight         309.31
_chemical_melting_point          136
_chemical_name_common            OXAZOLE
_chemical_name_systematic
(5-(3,4-dimethoxyphenyl)oxazol-2-yl)(phenyl)methanone
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2024-04-19 deposited with the CCDC.	2025-03-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.925(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.048(2)
_cell_length_b                   8.244(2)
_cell_length_c                   23.019(7)
_cell_measurement_reflns_used    9739
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.86
_cell_measurement_theta_min      2.55
_cell_volume                     1516.1(7)
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            31025
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.549
_exptl_absorpt_coefficient_mu    0.097
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             648
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethylacetate'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.499
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2644
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.132
_refine_ls_R_factor_all          0.1037
_refine_ls_R_factor_gt           0.0996
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0005P)^2^+9.1677P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2551
_refine_ls_wR_factor_ref         0.2573
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2436
_reflns_number_total             2644
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00039d2.cif
_cod_data_source_block           AKASPGNOX08_0ma_a
_cod_depositor_comments
'Adding full bibliography for 7160411--7160413.cif.'
_cod_original_cell_volume        1516.2(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7160413
_shelx_shelxl_version_number     2019/1
_shelx_res_checksum              1500