Synthesis of 6 H -1,2-oxazin-6-ones (microreview)
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Chemistry of Heterocyclic Compounds 2020, 56(10), 1280–1282
Synthesis of 6H-1,2-oxazin-6-ones (microreview) Alexey V. Nizovtsev1*, Mikhail S. Baranov1,2 1
Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997, Russia; е-mail: [email protected] 2 Pirogov Russian National Research Medical University, 1 Ostrovityanova St., Moscow 117997, Russia; е-mail: [email protected]
Submitted May 9, 2020 Accepted June 5, 2020
Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(10), 1280–1282
The microreview is devoted to the methods of synthesis of 6H-1,2-oxazin-6-ones published after 1999 and covers both universal and specific methods for the preparation of this class of compounds. Introduction Compounds containing the 6H-1,2-oxazin-6-one structural fragment have varied biological activity including antimicrobial1 and fungicidal.2 They are moderate cytotoxins against breast cancer cells3 and modulators of glucocorticoid receptors.4 Representatives of this class of
compounds are also found in nature.5 The growing interest in 6H-1,2-oxazin-6-ones over the past 20 years has led to the development of new methods for constructing this heterocycle which are summarized in this review.
Synthesis based on 4-oxocarboxylic acids and their derivatives The traditional approach to the synthesis of 6H-1,2-oxazin6-ones is based on the condensation of 4-oxocarboxylic acids with hydroxylamine.6 Usually, the reaction is carried out in pyridine,1,7,8 in EtOH in the presence of NaOAc,9 or in the melt.10 This method is most suitable to obtain benzo-1a,7 or heteroannulated1b,8 oxazinones 1. Often, 4-oxocarboxylic acids are replaced with the corresponding esters11,12 and amides.13,14 In such cases, the condensation is carried out in EtOH in the presence of Et3N11,14 or pyridine.13 Prepared oximes can also be introduced in the reaction;1,11 in this case, cyclization is carried out in acidic medium.1 The condensation of 4-oxocarboxylic acids and their derivatives with hydroxylamine is the basis of a number of other methods for the construction of oxazinones. For example, oxazinones can be prepared by catalytic carbonylation of aromatic oximes.15 Palladium-catalyzed transformations have also been used to introduce the carbonyl component into an aromatic acid molecule.16 Alexey Vadimovich Nizovtsev was born in 1976 in Slutsk, Belarus. In 1998, he graduated from the Department of Chemistry, Moscow State University. In 2002, he defended his PhD thesis. He works currently at the ShemyakinOvchinnikov Institute of Bioorganic Chemistry. His research interests include chemistry of heterocyclic compounds, peptide synthesis, olefin metathesis. 0009-3122/20/56(10)-1280©2020 Springer Science+Business Media, LLC
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Mikhail Sergeevich Baranov was born in 1986 in Moscow, Russia. In 2008, he graduated from the Chemistry Department, Moscow State University. In 2013, he defended his PhD thesis. Currently he is Head of the Group of chemistry of heterocyclic compo
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