Regioselective Syntheses of 2- and 4-Formylpyrido[2,1-b]benzoxazoles

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	Regioselective Syntheses of 2- and 4-Formylpyrido[2,1-b]benzoxazoles
	Li KL(李可来) ; Du ZB(杜宗波) ; Guo CC(郭灿城) ; Chen QY(陈庆云)
刊名	J. Org. Chem.
	2009
卷号	74 期号:9 页码:3286-3292
ISSN号	0022-3263
其他题名	区域选择性合成2-和4-醛基-吡啶并[2,1-b]苯并恶唑
通讯作者	郭灿城 ; 陈庆云
英文摘要	o-Acetaminophenols (2) reacted with Vilsmeier reagent under Meth-Cohn conditions to yield 2-formylpyrido[2,1-b]benzoxazoles (5) unexpectedly besides the known compounds 2-(benzoxazol-2'-yl)-3-dimethylaminoacroleins (4). Refluxing 4 in acetic anhydride gave 4-formylpyrido[2,1-b]benzoxazoles (6), an isomer of 5. Both 5a and 6a were structurally characterized by X-ray crystallography. A mechanism for the formation of 5 involving sequential chlorination, dimerization, intramolecular elimination of HCl to form the oxazole ring, formylation twice, and regioselective intramolecular nucleophilic cyclization to construct the pyridone ring is proposed.
学科主题	有机化学
收录类别	SCI
原文出处	http://dx.doi.org/10.1021/jo900267c
语种	英语
WOS记录号	WOS:000265554900006
公开日期	2013-01-17
内容类型	期刊论文
源URL	[http://202.127.28.38/handle/331003/13682]
专题	上海有机化学研究所_中科院有机氟化学重点实验室
推荐引用方式 GB/T 7714	Li KL,Du ZB,Guo CC,et al. Regioselective Syntheses of 2- and 4-Formylpyrido[2,1-b]benzoxazoles[J]. J. Org. Chem.,2009,74(9):3286-3292.
APA	李可来,杜宗波,郭灿城,&陈庆云.(2009).Regioselective Syntheses of 2- and 4-Formylpyrido[2,1-b]benzoxazoles.J. Org. Chem.,74(9),3286-3292.
MLA	李可来,et al."Regioselective Syntheses of 2- and 4-Formylpyrido[2,1-b]benzoxazoles".J. Org. Chem. 74.9(2009):3286-3292.