Reactions of isocyanates with methyl N-(cyanothioformyl)anthranilate

被引：11

作者：

Deck, LM ^{[1
]}

Papadopoulos, EP ^{[1
]}

Smith, KA ^{[1
]}

机构：

[1] Univ New Mexico, Dept Chem, Albuquerque, NM 87131 USA

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2003年 / 40卷 / 05期

关键词：

D O I：

10.1002/jhet.5570400522

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The triethylamine-catalyzed reactions of methyl N-(cyanothioformyl)anthranilate (1) with isocyanates result in cyclization involving the cyano group to form methyl 2-(4-imino-2-oxo-3-substituted-5-thioxoimidazolidin-1-yl)benzoates (4). Ring closure at the ester carbonyl to form 3-aryl-3,4-dihydro-4-oxoquinazoline-2-carbonitriles (8) is observed when the S-methyl derivative of 1 is allowed to react with aromatic amines.

引用

页码：885 / 893

页数：9

共 50 条

[1] REACTIONS OF N-BENZOYL ISOTHIOCYANATE WITH ANTHRANILIC ACID AND METHYL ANTHRANILATE
KAVALEK, J
KOTYK, M
ELBAHAIE, S
STERBA, V
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1981, 46 (01) : 246 - 255
[2] METABOLISM AND EXCRETION OF METHYL N-(O-AMINOPHENYL)-N-(3-DIMETHYLAMINOPROPYL) ANTHRANILATE IN DOG AND HUMAN
SMITH, DL
PULLIAM, AL
KO, H
JOURNAL OF PHARMACEUTICAL SCIENCES, 1967, 56 (07) : 815 - +
[3] MASS SPECTROMETRIC IDENTIFICATION OF METABOLITES OF METHYL N-(O-AMINOPHENYL)-N-(3-DIMETHYLAMINOPROPYL)ANTHRANILATE
SMITH, DL
GROSTIC, MF
JOURNAL OF MEDICINAL CHEMISTRY, 1967, 10 (03) : 375 - &
[4] N-(cyanothioformyl)indoline;: a new indoline ring forming reaction
Besson, T
Guillaumet, G
Lamazzi, C
Rees, CW
Thiéry, V
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (24): : 4057 - 4059
[5] REACTIONS OF METHYL ANTHRANILATE WITH ETHYL GAMMA-BROMOBUTYRATE
MCCALL, I
PROCTOR, GR
PURDIE, L
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1970, (08): : 1126 - &
[6] N-(TRIHALOMETHYLTHIO)-AMINOCARBONYL-ISOCYANATES
KUHLE, E
HAGEMANN, H
SYNTHESIS-STUTTGART, 1982, (11): : 949 - 949
[7] Structure of the product of the interaction of methyl anthranilate with N-(4,6-dimethylpyrimidin-2-yl)cyanamide
A. S. Shestakov
I. S. Bushmarinov
O. E. Sidorenko
A. Yu. Potapov
Kh. S. Shikhaliev
M. Yu. Antipin
Chemistry of Heterocyclic Compounds, 2011, 47 : 316 - 320
[8] STRUCTURE OF THE PRODUCT OF THE INTERACTION OF METHYL ANTHRANILATE WITH N-(4,6-DIMETHYLPYRIMIDIN-2-YL)CYANAMIDE
Shestakov, A. S.
Bushmarinov, I. S.
Sidorenko, O. E.
Potapov, A. Yu.
Shikhaliev, Kh. S.
Antipin, M. Yu.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2011, 47 (03) : 316 - 320
[9] Production of natural methyl anthranilate by microbial N-demethylation of N-methyl methyl anthranilate by the topsoil-isolated Bacterium bacillus megaterium
Taupp, M
Harmsen, D
Heckel, F
Schreier, P
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2005, 53 (24) : 9586 - 9589
[10] CYCLOADDITION REACTIONS OF ISOCYANATES . REACTION OF ARYL ISOCYANATES WITH N,N-DIMETHYLFORMAMIDE
ULRICH, H
TUCKER, B
STUBER, FA
SAYIGH, AAR
JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (10): : 3928 - &

← 1 2 3 4 5 →