The Vilsmeier-Haack formylation of 2,3-dihydro-4H-1,3-benzoxazin-4-ones and isomeric 1,2-dihydro-4H-3,1-benzoxazin-4-ones: an effective approach to functionalized 2H-/4H-chromenes and tetrahydroacridines

被引：14

作者：

Farat, Oleg K. ^{[1
,2
]}

Markov, Victor I. ^{[1
]}

Varenichenko, Svetlana A. ^{[1
]}

Dotsenko, Victor V. ^{[3
]}

Mazepa, Alexander V. ^{[4
]}

机构：

[1] Ukrainian State Univ Chem Technol, UA-49005 Dnepropetrovsk, Ukraine

[2] Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119991, Russia

[3] Kuban State Univ, Krasnodar 350040, Russia

[4] AV Bogatskii Inst Phys & Chem, UA-65080 Odessa, Ukraine

来源：

TETRAHEDRON | 2015年 / 71卷 / 34期

关键词：

Vilsmeier reagent; Rearrangement; Chromene derivatives; Tetrahydroacridine;

D O I：

10.1016/j.tet.2015.06.069

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We found that 1,3- and isomeric 3,1-benzoxazin-4-ones react with the Vilsmeier reagent in vastly different ways. Thus, either 2H- or 4H-chromenes were obtained in good yields when 1,3-benzoxazin-4-ones were reacted at 75-80 degrees C, while the formylation of 3,1-benzoxazines at ambient temperature leads to acridine-9-one or 9-chloroacridine derivatives, depending on the amount of Vilsmeier reagent and the nature of substrate. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：5554 / 5561

页数：8

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