[HYDROXY(TOSYLOXY)IODO]BENZENE IN ORGANIC SYNTHESIS: A FACILE SYNTHESIS OF FURO[3,2-c]COUMARINS USING α-TOSYLOXYKETONES

被引:10
作者
Prakash, Om [1 ]
Wadhwa, Deepak [2 ]
Hussain, Khalid [2 ]
Kumar, Ravi [3 ]
机构
[1] Kurukshetra Univ, Inst Pharmaceut Sci, Kurukshetra 136119, Haryana, India
[2] Kurukshetra Univ, Dept Chem, Kurukshetra 136119, Haryana, India
[3] Dyal Singh Coll, Dept Chem, Karnal, Haryana, India
关键词
Cyclocondensation; HTIB; 4-hydroxycoumarin; alpha-tosyloxyketones; COUMARIN DERIVATIVES; VITAMIN-K; 4-HYDROXYCOUMARINS; REARRANGEMENTS; CHEMISTRY; REAGENTS; ENTRY;
D O I
10.1080/00397911.2011.570471
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Facile synthesis of furo[3,2-c] coumarins (2a-g) via cyclocondensation of 4-hydroxycoumarin and -tosyloxyketones (1a-g) is described. A plausible mechanism involving C-C bond formation followed by 5-exo-tet cyclization is suggested.
引用
收藏
页码:2947 / 2951
页数:5
相关论文
共 26 条
[1]  
Acrell J., 1986, J ORG CHEM, V51, P3374
[2]   THE CHEMISTRY OF COUMARIN DERIVATIVES .6. DIELS-ALDER TRAPPING OF 3-METHYLENE-2,4-CHROMANDIONE - A NEW ENTRY TO SUBSTITUTED PYRANO[3,2-C]COUMARINS [J].
APPENDINO, G ;
CRAVOTTO, G ;
TOMA, L ;
ANNUNZIATA, R ;
PALMISANO, G .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (19) :5556-5564
[3]   Oxidative addition of 4-hydroxycoumarin to alkenes. An expeditious entry to 2,3-dihydro-4H-furo-[3,2-c][1]benzopyran-4-ones [J].
Appendino, G ;
Cravotto, G ;
Palmisano, G ;
Annunziata, R .
SYNTHETIC COMMUNICATIONS, 1996, 26 (18) :3359-3371
[4]   PREFERENCE FOR 6-EXO-TRIGONAL CLOSURES OF "OMEGA-HYDROXY-ALPHABETA-UNSATURATED ESTERS [J].
BALDWIN, JE ;
REISS, JA .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (03) :77-77
[5]   RULES FOR RING-CLOSURE [J].
BALDWIN, JE .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :734-736
[6]  
Darbarwar M., 1993, INDIAN J CHEM, V11, P115
[7]  
Das Gupta K., 1981, INDIAN J CHEM B, V20, P511
[8]   A NOVEL SYNTHESIS OF 2-IMINO-4-THIAZOLINES VIA ALPHA-BROMOKETIMINES [J].
DEKIMPE, N ;
BOELENS, M ;
DECLERCQ, JP .
TETRAHEDRON, 1993, 49 (16) :3411-3424
[9]  
Feuer G, 1974, Prog Med Chem, V10, P85, DOI 10.1016/S0079-6468(08)70267-4
[10]   3-benzoyl-3,4-dihydro-2H,5H-1-benzopyrano[4,3-b]pyran-5-ones by condensation of 4-hydroxycoumarins with enone Mannich bases [J].
Girreser, U ;
Heber, D ;
Schütt, M .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1998, 35 (06) :1455-1460