[5C+1S] annulation: A facile and efficient synthetic route toward functionalized 2,3-dihydrothiopyran-4-ones

被引:64
作者
Bi, XH [1 ]
Dong, DW [1 ]
Li, Y [1 ]
Liu, Q [1 ]
Zhang, Q [1 ]
机构
[1] NE Normal Univ, Dept Chem, Changchun 130024, Peoples R China
关键词
D O I
10.1021/jo052032g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A facile and efficient synthetic route toward highly substituted 2,3-dihydrothiopyran-4-ones 2 has been developed via a formal [5C + 1S] annulation of readily available alpha-alkenoyl ketene-(S,S)-acetals 1 with sodium sulfide nonahydrated salt (Na(2)S(.)9H(2)O) and utilized in the synthesis of 2-(4-chlorophenyl)-6-(morpholin-4-yl)-4H-thiopyran-4-one 51, an inhibitor of DNA-dependent protein kinase (DNA-PK).
引用
收藏
页码:10886 / 10889
页数:4
相关论文
共 47 条
[1]  
AUGUSTIN M, 1977, SYNTHESIS-STUTTGART, P472
[2]  
BARLUENGA J, 1991, SYNLETT, P487
[3]   [5+1] annulation: A synthetic strategy for highly substituted phenols and cyclohexenones [J].
Bi, XH ;
Dong, DW ;
Liu, Q ;
Pan, W ;
Zhao, L ;
Li, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4578-4579
[4]   THE SYNTHESIS OF 2,3-DISUBSTITUTED CYCLOPENTENONES USING THE RAMBERG BACKLUND REACTION IN CONJUNCTION WITH ORGANOCOPPER CHEMISTRY [J].
CASY, G ;
TAYLOR, RJK .
TETRAHEDRON, 1989, 45 (02) :455-466
[5]   FACILE RAMBERG-BACKLUND REACTIONS FOR THE SYNTHESIS OF 2,3-DISUBSTITUTED CYCLOPENTENONES - A SHORT SYNTHETIC ROUTE TO TETRAHYDRODICRANENONE-B [J].
CASY, G ;
TAYLOR, RJK .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (07) :454-455
[6]   THE PREPARATION OF THIATHROMBOXANE ANALOGS AND A FORMAL TOTAL SYNTHESIS OF DITHIATHROMBOXANE-A2 BASED ON CONJUGATE ADDITION-REACTIONS OF THIIN-4-ONES [J].
CASY, G ;
LANE, S ;
TAYLOR, RJK .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (08) :1397-1404
[7]   SYNTHESIS OF 4H-THIOPYRAN-4-ONES [J].
CHEN, CH ;
REYNOLDS, GA ;
VANALLAN, JA .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (16) :2777-2778
[8]   SYNTHESIS OF 2-PHENYL-4H-THIOPYRAN-4-ONE [J].
CHEN, CH ;
DONEY, JJ ;
REYNOLDS, GA .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (22) :4604-4605
[9]  
CHOI EB, 1991, SYNTHESIS-STUTTGART, P15
[10]   [5C+1N] Annulation: a novel synthetic strategy for functionalized 2,3-dihydro-4-pyridones [J].
Dong, DW ;
Bi, XH ;
Liu, Q ;
Cong, FD .
CHEMICAL COMMUNICATIONS, 2005, (28) :3580-3582