ARTIKEL
Switchable Reaction of p‐Toluenesulfonyl Hydrazide With N‐Heteroaryl Ketones: Base‐Controlled Selective Synthesis of N‐Heteroaryl Alcohols and [1, 2, 3]‐Triazoloheteroarenes
![Switchable Reaction of p‐Toluenesulfonyl Hydrazide With N‐Heteroaryl Ketones: Base‐Controlled Selective Synthesis of N‐Heteroaryl Alcohols and [1, 2, 3]‐Triazoloheteroarenes](/_next/image?url=https%3A%2F%2Fcdn.gdch.de%2Fprod%2Fswitchable_reaction_of_ptoluenesulfonyl_hydrazide_with_nheteroaryl_ketones_basecontrolled_selective_ajoc_aa8c24ab36.jpeg&w=3840&q=75)
Von Wiley-VCH zur Verfügung gestellt
A switchable reaction of p-toluenesulfonyl hydrazide with N-heteroaryl ketones has been developed to synthesize N-heteroaryl alcohols and [1, 2, 3]-triazoloheteroarenes. p-Toluenesulfonyl hydrazide was found to be a reducing agent in the presence of Et3N, whereas [1, 2, 3]-triazoloheteroarenes were obtained when NaOH was applied as a base.
Abstract
A novel switchable reaction of p-toluenesulfonyl hydrazide with N-heteroaryl ketones has been developed to synthesize N-heteroaryl alcohols and [1, 2, 3]-triazoloheteroarenes. p-Toluenesulfonyl hydrazide was found to be an efficient reducing agent for N-heteroaryl ketones in the presence of Et3N. A cascade cyclization reaction occurred when NaOH was applied as a base.
![Switchable Reaction of p‐Toluenesulfonyl Hydrazide With N‐Heteroaryl Ketones: Base‐Controlled Selective Synthesis of N‐Heteroaryl Alcohols and [1, 2, 3]‐Triazoloheteroarenes](/_next/image?url=https%3A%2F%2Fcdn.gdch.de%2Fprod%2Finvestigation_of_phosphine_ligand_effect_on_tunable_optical_property_of_novel_coumarintriphenylimino_ajoc_53a3435d3c.jpeg&w=256&q=75)
![Switchable Reaction of p‐Toluenesulfonyl Hydrazide With N‐Heteroaryl Ketones: Base‐Controlled Selective Synthesis of N‐Heteroaryl Alcohols and [1, 2, 3]‐Triazoloheteroarenes](/_next/image?url=https%3A%2F%2Fcdn.gdch.de%2Fprod%2Fsynthesis_of_diaryl_thiosulfonates_via_electrochemical_cascade_sscoupling_using_arylsulfonyl_chlorid_ajoc_521e1b834a.jpeg&w=256&q=75)
![Switchable Reaction of p‐Toluenesulfonyl Hydrazide With N‐Heteroaryl Ketones: Base‐Controlled Selective Synthesis of N‐Heteroaryl Alcohols and [1, 2, 3]‐Triazoloheteroarenes](/_next/image?url=https%3A%2F%2Fcdn.gdch.de%2Fprod%2Fsynthesis_of_nsubstituted_4pyridones_from_skipped_diynones_via_intramolecular_base_or_agicatalyzed_h_ajoc_bb6fb124dc.jpeg&w=256&q=75)
![Switchable Reaction of p‐Toluenesulfonyl Hydrazide With N‐Heteroaryl Ketones: Base‐Controlled Selective Synthesis of N‐Heteroaryl Alcohols and [1, 2, 3]‐Triazoloheteroarenes](/_next/image?url=https%3A%2F%2Fcdn.gdch.de%2Fprod%2Ffluoranthene_embedded_doubly_fused_expanded_porphyrin_ajoc_2847a15b6f.jpeg&w=256&q=75)
![Switchable Reaction of p‐Toluenesulfonyl Hydrazide With N‐Heteroaryl Ketones: Base‐Controlled Selective Synthesis of N‐Heteroaryl Alcohols and [1, 2, 3]‐Triazoloheteroarenes](/_next/image?url=https%3A%2F%2Fcdn.gdch.de%2Fprod%2Fsynthesis_of_multisubstituted_pyranoindol1ones_using_iridiumcatalyzed_intramolecular_ch_amination_of_ajoc_549698a30b.jpeg&w=256&q=75)
