ENAMINO KETONES AS PRECURSORS OF FUNCTIONALIZED 2H-THIOPYRANS AND THIOPYRANO[2,3-C]BENZOTHIOPYRANS AND THIOPYRANO[3,2-B]BENZOTHIOPYRANS

被引:18
作者
GABBUTT, CD [1 ]
HEPWORTH, JD [1 ]
HERON, BM [1 ]
机构
[1] UNIV CENT LANCASHIRE, DEPT CHEM, PRESTON PR1 2HE, ENGLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 20期
关键词
D O I
10.1039/p19920002603
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Oxo enamino ketones obtained by treating active methylene compounds with N,N-dimethylformamide dimethyl acetal yield novel 2H-thiopyrans in a regioselective one pot thionation-[4 + 2]-cycloaddition sequence. Application of similar methodology to thiochroman-3-ones affords novel thiopyrano[2,3-c][1]benzothiopyrans and the [3,2-b] isomers.
引用
收藏
页码:2603 / 2608
页数:6
相关论文
共 49 条
[1]   CHEMISTRY OF FORMAMIDE ACETALS [J].
ABDULLA, RF ;
BRINKMEYER, RS .
TETRAHEDRON, 1979, 35 (14) :1675-1735
[2]  
ARNOLDI A, 1908, SYNTHESIS-STUTTGART, P856
[3]   DIELS-ALDER CYCLOADDITION REACTIONS OF ENAMINOTHIONES WITH NITROALKENES [J].
BARUAH, PD ;
MUKHERJEE, S ;
MAHAJAN, MP .
TETRAHEDRON, 1990, 46 (06) :1951-1962
[4]   SYNTHESIS OF 1-(1,1-DIMETHYLETHYL)-1H-PYRAZOLE-4-CARBOXYLATE ESTER DERIVATIVES [J].
BECK, JR ;
LYNCH, MP .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1987, 24 (03) :693-695
[5]  
BOGER DL, 1987, HETERO DIELSALDER ME, P214
[6]  
BRADAMANTE S, 1972, J CHEM SOC P1, P289
[7]   SYNTHESIS OF 6-METHOXY-2,2-DIMETHYL-2H-1-BENZOTHIOPYRAN AND 6,7-DIMETHOXY-2,2-DIMETHYL-2H-1-BENZOTHIOPYRAN, SULFUR ANALOGS OF PRECOCENE-I AND PRECOCENE-II [J].
CAMPS, F ;
COLOMINA, O ;
COLL, J ;
MESSEGUER, A .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1983, 20 (04) :1115-1117
[8]   THIONATION REACTIONS OF LAWESSON REAGENTS [J].
CAVA, MP ;
LEVINSON, MI .
TETRAHEDRON, 1985, 41 (22) :5061-5087
[9]   THIOPYRANOTHIOPYRAN CHEMISTRY .5. SYNTHESIS OF DIBENZO[B,G]THIOPYRANO[3,2-B]THIOPYRAN-6,12-DIONE (THIOEPINDOLIDIONE) [J].
CHEN, CH ;
FOX, JL .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (19) :3592-3595
[10]   THIOPYRANOTHIOPYRAN CHEMISTRY .1. SYNTHESIS OF 1,3,5,7-TETRAPHENYLTHIOPYRANO[4,3-C]THIOPYRAN 2,2,6,6-TETRAOXIDE [J].
CHEN, CH ;
REYNOLDS, GA ;
SMITH, DL ;
FOX, JL .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (26) :5136-5143