N,N-dialkyl-N′-chlorosulfonyl chloroformamidines in heterocyclic synthesis.: IV.: 3-dialkylamino-1,1,8-trioxo-1H-1λ6-pyrano[3,4-e][1,4,3]oxathiazines

被引：8

作者：

Cablewski, Teresa ^{[1
]}

Francis, Craig L. ^{[1
]}

Liepa, Andris J. ^{[1
]}

机构：

[1] CSIRO Mol & Hlth Technol, Clayton, Vic 3168, Australia

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 2007年 / 60卷 / 02期

关键词：

D O I：

10.1071/CH06368

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

N,N-dialkyl-N'-chlorosulfonylchloroformamidines 1 reacted regioselectively with 4-hydroxy-2-pyrone derivatives 2 to give 3-dialkylamino-1,1,8-trioxo-1H-1 lambda(6)-pyrano[3,4-e][1,4,3] oxathiazines 3. Dichloride 1b reacted regioselectively with 1,3-dimethylbarbituric acid 10 to give 3-diethylamino-5,7-dimethyl-1,1,6,8-tetraoxo-1H-1 lambda(6)-pyrimido[5,4-e][ 1,4,3] oxathiazine 11. The compounds 3 and 11 are derivatives of new ring systems.

引用

页码：113 / 119

页数：7

共 12 条

[1] N,N-dialkyl-N′-chlorosulfonyl chloroformamidines in heterocyclic synthesis.: III.: Pyrido- and pyridazo-fused [1,2,4,6]thiatriazine dioxides [J].

Cablewski, Teresa ;

Carter, Erin J. ;

Francis, Craig L. ;

Liepa, Andris J. ;

Perkins, Michael V. .

AUSTRALIAN JOURNAL OF CHEMISTRY, 2007, 60 (02) :105-112

[2] ENOL ETHERS .17. ACYLATION OF TRIMETHYLSILYL ENOL ETHERS WITH MALONYL DICHLORIDE - SYNTHESIS OF 4-HYDROXY-2H-PYRAN-2-ONES [J].

EFFENBERGER, F ;

ZIEGLER, T ;

SCHONWALDER, KH ;

KESMARSZKY, T ;

BAUER, B .

CHEMISCHE BERICHTE-RECUEIL, 1986, 119 (11) :3394-3404

[3] N,N-Dialkyl (N′-chlorosulfonyl)chloroformamidines in heterocyclic synthesis.: I.: The preparation of [1,2,3,5]thiatriazole and [1,3,2,4]oxathiadiazole derivatives [J].

Fallon, GD ;

Jahangiri, S ;

Liepa, AJ ;

Woodgate, RCJ .

AUSTRALIAN JOURNAL OF CHEMISTRY, 2005, 58 (05) :332-338

[4]

FALLON GD, AUST J CHEM, V891, P5, DOI DOI 10.1071/CH05070

[5] THE SYNTHESIS OF CERTAIN 5-AMINOTETRAZOLE DERIVATIVES .1. THE ACTION OF HYDRAZOIC ACID ON SOME DIALKYLCYANAMIDES [J].

GARBRECHT, WL ;

HERBST, RM .

JOURNAL OF ORGANIC CHEMISTRY, 1953, 18 (08) :1003-1013

[6] THE SYNTHESIS OF DIHYDRO-1,2,3,5-THIATRIAZOLE-1,1-DIOXIDES .2. [J].

KNOLLMULLER, M ;

KOSMA, P .

MONATSHEFTE FUR CHEMIE, 1985, 116 (11) :1321-1327

[7]

Markovskii L. N., 1973, J ORG CHEM USSR, V9, P644

[8]

MARKOVSKII LN, 1974, J ORG CHEM USSR, V10, P492

[9] MECHANISM OF ACYLATION OF DILITHIUM SALTS OF BETA-KETO-ESTERS - AN EFFICIENT SYNTHESIS OF ANIBINE [J].

NARASIMHAN, NS ;

AMMANAMANCHI, R .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :3945-3947

[10] REACTIONS WITH DIALKYLCYANAMIDES - REACTION OF DIALKYLCYANAMIDES WITH SULFUR OR PHOSPHORUS HALIDES - SYNTHESIS OF SUBSTITUTED CHLOROFORMAMIDINES [J].

SCHINDLER, N .

CHEMISCHE BERICHTE-RECUEIL, 1973, 106 (01) :56-61

← 1 2 →