DBU mediated one-pot synthesis of triazolo triazines via Dimroth type rearrangement. Issue 4 (12th January 2022)

• Record Type: Journal Article
• Authors: Ganai, Ab Majeed; Pathan, Tabasum Khan; Sayyad, Nisar; Kushwaha, Babita; Kushwaha, Narva Deshwar; Tzakos, Andreas G.; Karpoormath, Rajshekhar
• Is Part Of: RSC advances. Volume 12:Issue 4(2022)
• Page Start: 2102
• Page End: 2106
• Publication Date: 2022-01-12
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d1ra07749j
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : We demonstrate a simple yet efficient one-pot synthesis of two triazolotriazine isomers via DBU mediated Dimroth type rearrangement with excellent yields. Abstract : Herein we report an efficient one-pot synthesis of [1, 2, 4]triazolo[1, 5 a ][1, 3, 5]triazines from commercially available substituted aryl/heteroaryl aldehydes and substituted 2-hydrazinyl-1, 3, 5-triazines via N -bromosuccinimide (NBS) mediated oxidative C–N bond formation. Isomerisation of [1, 2, 4]triazolo[4, 3- a ][1, 3, 5]triazines to [1, 2, 4]triazolo[1, 5- a ][1, 3, 5]triazines is driven by 1, 8-diazabicyclo[5.4.0]undec-7-ene (DBU) affording both isomers with good to excellent yields (70–96%).