The Construction of Polycyclic Pyridones via Ring-Opening Transformations of 3-hydroxy-3,4-dihydropyrido[2,1-c][1,4]oxazine-1,8-diones

被引:6
|
作者
Viktorova, Viktoria V. [1 ]
Steparuk, Elena V. [1 ]
Obydennov, Dmitrii L. [1 ]
Sosnovskikh, Vyacheslav Y. [1 ]
机构
[1] Ural Fed Univ, Inst Nat Sci & Math, 51 Lenina Ave, Ekaterinburg 620000, Russia
来源
MOLECULES | 2023年 / 28卷 / 03期
关键词
4-pyridone; oxazinone; ring-opening; benzimidazole; aldehyde-lactol tautomerism; ammonium acetate; ETHYL; 5-ACYL-4-PYRONE-2-CARBOXYLATES; FINAL FORMS; DOLUTEGRAVIR; EFFICIENT; 6-ARYL; ACIDS;
D O I
10.3390/molecules28031285
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
This work describes the synthesis of 3-hydroxy-3,4-dihydropyrido[2,1-c][1,4]oxazine-1,8-diones, their tautomerism, and reactivity towards binucleophiles. These molecules are novel and convenient building-blocks for the direct construction of biologically important polycyclic pyridones via an oxazinone ring-opening transformation promoted with ammonium acetate or acetic acid. In the case of o-phenylenediamine, partial aromatization of the obtained heterocycles proceeded to form polycyclic benzimidazole-fused pyridones (33-91%).
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页数:13
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