Dichotomy in the reactivity of 2-methyltetrahydroquinazoline 1-oxides towards aldehydes: An unprecedented condensation with simultaneous reduction of the N-oxide fragment. Issue 11 (12th March 2020)

• Record Type: Journal Article
• Authors: Sedenkova, Kseniya N.; Terekhin, Alexey V.; Abdrashitova, Irina V.; Vasilenko, Dmitry A.; Sadovnikov, Kirill S.; Gracheva, Yulia A.; Grishin, Yuri K.; Holt, Tina; Kutateladze, Andrei G.; Kuznetsova, Tamara S.; Milaeva, Elena R.; Averina, Elena B.
• Is Part Of: Tetrahedron letters. Volume 61:Issue 11(2020)
• Publication Date: 2020-03-12
• Subjects: Condensation -- N-Oxides -- Pyrimidines -- Reduction; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2020.151605
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Cyanopyrimidine N -oxides react with aldehydes giving unexpected condensation products. The condensation proceeds employing methylene group instead of methyl. The condensation proceeds with simultaneous reduction of N -oxide. Abstract: An unusual condensation reaction of 2-methyltetrahydroquinazoline N -oxides with aromatic aldehydes was found. The reaction of 4-cyano substituted heterocycles as well as the use of microwave irradiation for 4-morpholinyl substituted heterocycles resulted in the condensation engaging the methylene group of the tetrahydroquinazoline fragment with simultaneous deoxygenation of the N -oxide. A preparative approach towards previously unknown pyrimidine-containing conjugated molecules was developed based on this process.