ACID-CATALYZED CYCLIZATION OF ALKOXYACRYLOYLUREAS TO 2,4(1H,3H)PYRIMIDINEDIONES

被引：51

作者：

SHEALY, YF ^{[1
]}

ODELL, CA ^{[1
]}

机构：

[1] SO RES INST, KETTERING MEYER LAB, BIRMINGHAM, AL 35205 USA

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 1976年 / 13卷 / 05期

关键词：

D O I：

10.1002/jhet.5570130521

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1-Phenylthymine and the carbocyclic analog of thymidine were obtained in yields of 84-87% by cyclizing the appropriate 3-methoxy-2-methylacryloylureas in dilute H2SO4. High yields of 1-phenylthymine also resulted when the cyclization was carried out in trifluoroacetic acid, in acetic acid containing toluenesulfonic acid (TSA), or by fusiobpn of the urea with a catalytic amount of TSA. The typical aqueous-alkali catalyzed cyclizations gave lower yields of the 2 thymines, and cleavage of the acryloylureas occurred. Cyclization in concentrated aqueous ammonia produced high yields of both thymine derivatives.

引用

页码：1041 / 1047

页数：7

共 36 条

[1] PURINES, PYRIMIDINES, AND GLYOXALINES .6. SOME 5-ARYL(OR ALKYL)SULPHONYLURACILS [J].

ATKINSON, MR ;

SHAW, G ;

SUGOWDZ, G .

JOURNAL OF THE CHEMICAL SOCIETY, 1957, (JUL) :3207-3209

[2] PURINES, PYRIMIDINES AND GLYOXALINES .5. NEW SYNTHESES OF URACILS AND OROTIC ACIDS [J].

ATKINSON, MR ;

MAGUIRE, MH ;

RALPH, RK ;

SHAW, G ;

WARRENER, RN .

JOURNAL OF THE CHEMICAL SOCIETY, 1957, (MAY) :2363-2368

[3] PURINES, PYRIMIDINES, AND GLYOXALINES .4. CYANOURACILS FROM AMINES AND AMINO-ACIDS [J].

ATKINSON, MR ;

SHAW, G ;

WARRENER, RN .

JOURNAL OF THE CHEMICAL SOCIETY, 1956, (NOV) :4118-4123

[4] PURINES, PYRIMIDINES, AND GLYOXALINES .3. A NEW SYNTHESIS OF 2-THIOURACILS [J].

ATKINSON, MR ;

SHAW, G ;

SCHAFFNER, K ;

WARRENER, RN .

JOURNAL OF THE CHEMICAL SOCIETY, 1956, (OCT) :3847-3849

[5] PURINES, PYRIMIDINES, AND IMIDAZOLES .41. GLYCOFURANOSYLAMINES DERIVED FROM D-XYLOSE, D-GLUCOSE, D-MANNOSE AND L-RHAMNOSE AND THEIR USE IN SYNTHESIS OF PYRIMIDINE AND IMIDAZOLE NUCLEOSIDES [J].

CUSACK, NJ ;

ROBINSON, DH ;

RUGG, PW ;

SHAW, G ;

LOFTHOUSE, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (01) :73-81

[6] PURINES, PYRIMIDINES, AND IMIDAZOLES .40. NEW SYNTHESIS OF A D-RIBOFURANOSYLAMINE DERIVATIVE AND ITS USE IN SYNTHESIS OF PYRIMIDINE AND IMIDAZOLE NUCLEOSIDES [J].

CUSACK, NJ ;

HILDICK, BJ ;

ROBINSON, DH ;

RUGG, PW ;

SHAW, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (16) :1720-1731

[7] NON-GLYCOSIDIC ANALOGS OF NUCLEOSIDES .3. 1-(2'-METHYLENETETRAHYDROFURYL) URACIL 1-(2'-METHYLENETETRAHYDROFURYL)THYMINE AND 1-(2'-METHYLENETETRAHYDROFURYL) CYTOSINE . 1-(2'-R-METHYLENETETRAHYDROFURYL) URACIL [J].

DEFAYE, J ;

NAUMBERG, M ;

REYNERS, T .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1969, 6 (02) :229-&

[8]

DEKONING H, 1971, RECL TRAV CHIM PAY-B, V90, P874

[9] PURINES PYRIMIDINES AND IMIDAZOLES .21. SOME URACILS AND ISOCYTOSINES [J].

DEWAR, JH ;

SHAW, G .

JOURNAL OF THE CHEMICAL SOCIETY, 1965, (MAR) :1642-&

[10] PURINES, PYRIMIDINES, AND IMIDAZOLES .17. A SYNTHESIS OF WILLARDIINE [J].

DEWAR, JH ;

SHAW, G .

JOURNAL OF THE CHEMICAL SOCIETY, 1962, (FEB) :583-&

← 1 2 3 4 →