REACTIONS OF ISOCYANATES WITH 1-CYANOTHIOFORMANILIDE

被引：33

作者：

PAPADOPOULOS, EP

机构：

[1] Department of Chemistry, University of New Mexico, Albuquerque

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 22期

关键词：

D O I：

10.1021/jo01336a023

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The triethylamine-catalyzed reaction of 1-cyanothioformanilide (2) with isocyanates forms 1-substituted 5-imino-3-phenyl-4-thioxo-2-imidazolidinones 5 in excellent yield. Compounds 5 are converted by aqueous acid into 3-phenyl-4-thioxo-2, 5-imidazolidinediones 6 and are oxidized by H2O2 in HOAc to 3-phenylimidazolidinetriones 4. Condensation of 5 with o-phenylenediamine yields lH-imidazo[4, 5-6]quinoxalin-2(3AH)-ones 8. Upon being heated 2 reacts with 2 equiv of isocyanate to form 5-carbamoylimino-3-phenyl-4-thioxo-2-imidazolidinones 7. © 1979, American Chemical Society. All rights reserved.

引用

页码：3858 / 3861

页数：4

共 15 条

[1]

BILTZ H, 1913, CHEM BER, V46, P1387

[2] STUDIES IN THE AZOLE SERIES .33. THE INTERACTION OF ALPHA-AMINO-NITRILES AND ALKYL OR ARYL ISOCYANATES [J].

COOK, AH ;

HUNTER, GD .

JOURNAL OF THE CHEMICAL SOCIETY, 1952, (OCT) :3789-3796

[3]

DE PK, 1927, Q J INDIAN CHEM SOC, V4, P531

[4]

DIECKMANN W, 1905, CHEM BER, V38, P2977

[5]

DIECKMANN W, 1907, CHEM BER, V40, P13737

[6]

Iijima C, 1967, Yakugaku Zasshi, V87, P164

[7]

MALACHOWSKI R, 1951, ROCZNIKI CHEM, V25, P35

[8] REACTIONS OF ISOCYANATES WITH CYANOHYDRINS . SYNTHESIS OF 2,4-OXAZOLIDINEDIONES AND 1,3-DISUBSTITUTED PARABANIC ACIDS [J].

PATTON, TL .

JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (02) :383-&

[9]

PERRONNET J, 1970, B SOC CHIM FR, P1168

[10]

PIOZZI F, 1957, ATTI ACCAD NAZ LINCE, V22, P629

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