SYNTHESIS OF PYRIMIDO[2,1-B]THIAZIN-6-ONE BY RETRO DIELS-ALDER REACTION

被引:17
作者
FULOP, F
HUBER, I
SZABO, A
BERNATH, G
SOHAR, P
机构
[1] ALBERT SZENT GYORGYI MED UNIV,INST PHARMACEUT CHEM,POB 121,H-6701 SZEGED,HUNGARY
[2] EGIS PHARMACEUT,DEPT SPECTROSCOP,H-1475 BUDAPEST,HUNGARY
关键词
THIAZOLO[2,3-B]QUINAZOLIN-5-ONE; THIAZINO[2,3-B]QUINAZOLIN-6-ONE; RETRODIENE DECOMPOSITION; THIAZOLO[3,2-A]PYRIMIDIN-5-ONE; PYRIMIDO[2,1-B]THIAZIN-6-ONE;
D O I
10.1016/S0040-4020(01)88290-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first mild retrodiene processes resulting in bicyclic heterocycles are described. From norbornene diexo- and diendo-beta-amino acids with chloroalkyl isothiocyanates, compounds 3-6 were prepared, which, by retrodiene decomposition, furnished 7 and 8.
引用
收藏
页码:7673 / 7676
页数:4
相关论文
共 19 条
[1]   STEREOCHEMICAL STUDIES .107. SATURATED HETEROCYCLES .111. PREPARATION OF URACILS VIA CYCLOREVERSION OF NORBORNENE-FUSED PYRIMIDINEDIONES [J].
BERNATH, G ;
STAJER, G ;
SZABO, AE ;
SZOKEMOLNAR, Z ;
SOHAR, P ;
ARGAY, G ;
KALMAN, A .
TETRAHEDRON, 1987, 43 (08) :1921-1930
[2]   DIE DARSTELLUNG VON BETA-CHLOR-ATHYL-AMIDEN UND BIS-[BETA-CHLOR-ATHYL]-AMIDEN VERSCHIEDENER SAUREN [J].
BRINTZINGER, H ;
PFANNSTIEL, K ;
KODDEBUSCH, H .
CHEMISCHE BERICHTE-RECUEIL, 1949, 82 (4-5) :389-399
[3]   SYNTHESIS AND REACTIONS OF THIAZOLIDINO[3,2-A]PYRIMIDINES [J].
BROWN, GR ;
DYSON, WR .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (08) :1527-&
[4]   REACTION OF ANTHRANILAMIDE WITH ISOTHIOCYANATE - A ONE-POT SYNTHESIS OF 2,3-DIHYDRO-5H-THIAZOLO[2,3-B]QUINAZOLIN-5-ONE [J].
CHERN, JW ;
LIU, KC ;
SHISH, FJ ;
CHAN, CH .
ARCHIV DER PHARMAZIE, 1987, 320 (12) :1276-1277
[5]  
KINOSHITA T, 1987, CHEM PHARM BULL, V35, P90
[6]   SYNTHESIS AND ANTIALLERGY ACTIVITY OF 5-OXO-5H-THIAZOLO[2,3-B]QUINAZOLINECARBOXYLIC ACIDS [J].
LEMAHIEU, RA ;
CARSON, M ;
WELTON, AF ;
BARUTH, HW ;
YAREMKO, B .
JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (01) :107-110
[7]   SYNTHESIS AND ANTIHYPERTENSIVE ACTIVITY OF SOME QUINAZOLINONE DERIVATIVES [J].
LIU, KC ;
HSU, LY .
ARCHIV DER PHARMAZIE, 1985, 318 (06) :502-505
[8]   NEW ONE-STEP SYNTHESIS OF 2,3-DIHYDRO-5H-THIAZOLO[2,3-B]QUINAZOLIN-5-ONE AND 3,4-DIHYDRO-2H,6H[1,3]THIAZINO[2,3-B]QUINAZOLIN-6-ONE [J].
PAYNE, LG ;
PRZYTYCKI, J ;
PATCHETT, AA ;
WU, MT .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1979, 16 (02) :391-391
[9]  
PECORARI P, 1989, J HETEROCYCLIC CHEM, V26, P1701
[10]   ELECTRON IONIZATION MASS-SPECTRA OF SOME CYCLOHEXANE FUSED 2-N-PHENYLIMINOPERHYDRO-1,3-OXAZINES AND RELATED THIAZINES [J].
PIHLAJA, K ;
LOTJONEN, L ;
FULOP, F ;
BERNATH, G ;
VAINIOTALO, P .
RAPID COMMUNICATIONS IN MASS SPECTROMETRY, 1990, 4 (08) :279-282