SYNTHESIS OF N3-SUBSTITUTED QUINAZOLINE-2,4-DIONES VIA C-4 AMINATION-CYCLIZATION OF ISATOIC ANHYDRIDES

被引：1

作者：

Wiriya, Nittaya ^{[1
]}

Yamano, Dolnapa ^{[1
]}

Hongsibsong, Surat ^{[2
,3
]}

Pattarawarapan, Mookda ^{[1
,2
,4
]}

Phakhodee, Wong ^{[1
,2
,4
]}

机构：

[1] Chiang Mai Univ, Fac Sci, Dept Chem, Chiang Mai 50200, Thailand

[2] Chiang Mai Univ, Environm Occupat Hlth Sci & Non Communicable Dis, Chiang Mai 50200, Thailand

[3] Chiang Mai Univ, Res Inst Hlth Sci, Sch Hlth Sci Res, Chiang Mai 50200, Thailand

[4] Chiang Mai Univ, Fac Sci, Res Ctr Chem Dev Hlth Promoting Prod Northern Res, Chiang Mai 50200, Thailand

来源：

HETEROCYCLES | 2022年 / 105卷 / 01期

关键词：

ONE-POT SYNTHESIS; MEDIATED SYNTHESIS; DERIVATIVES; EFFICIENT; QUINAZOLINE-2,4(1H,3H)-DIONES; 2,4(1H,3H)-QUINAZOLINEDIONE; ISOCYANIDES; CO2; CYCLOCARBONYLATION; INHIBITORS;

D O I：

10.3987/COM-22-S(R)10

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A direct approach for the synthesis of N3-substituted quinazoline-2,4-diones via condensation of isatoic anhydrides with amines mediated by Ph3P-I-2 was reported. Instead of the expected benzoxazinones, the reaction proceeds with an amine attack at the C-4 position of isatoic anhydrides leading to quinazoline-2,4-diones upon heating in the presence of base. This one-pot process enables a rapid construction of a broad range of quinazoline-2,4-dione derivatives using simple, readily available, and low-cost reagents with no extra carbonylating agent needed.

引用

页码：556 / 565

页数：10

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