An unusual ring expansion from the Zav'yalov pyrrole synthesis:: formation of oxacino[2,3-c]pyrroles

被引:10
作者
Gabbutt, CD
Hepworth, JD
Heron, BM [1 ]
Elsegood, MRJ
Clegg, W
机构
[1] Univ Hull, Dept Chem, Hull HU6 7RX, N Humberside, England
[2] Univ Newcastle Upon Tyne, Dept Chem, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England
关键词
D O I
10.1039/a809033e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Enamino acids 2 and 5 undergo a facile cyclisation to afford the pyrrole 3 and isoindole 6 ring systems; a novel two atom ring expansion ensues when derivatives 5b,d are subjected to the cyclisation conditions, resulting in the formation of the new oxacino[2,3-c]pyrrole system, the structure of which is confirmed by X-ray crystallography.
引用
收藏
页码:289 / 290
页数:2
相关论文
共 27 条
[1]   DIFFERENTIAL REACTIVITY OF BETA-AMINO ENONES AND 3-DIMETHYLAMINOACRYLALDEHYDE TOWARDS ALPHA-AMINO DERIVATIVES [J].
ALBEROLA, A ;
ANDRES, JM ;
GONZALEZ, A ;
PEDROSA, R ;
VICENTE, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (10) :2681-2685
[2]   SOME KINETIC AND MECHANISTIC STUDIES OF DAKIN-WEST REACTION [J].
ALLINGER, NL ;
WANG, GL ;
DEWHURST, BB .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (12) :1730-1735
[3]   TETRAMETHYLAMMONIUM GLYCINATE - A NEW REAGENT FOR IMPROVED PYRROLE SYNTHESIS BY [3+2] CYCLIZATION [J].
ANSARI, MA ;
CRAIG, JC .
SYNTHETIC COMMUNICATIONS, 1991, 21 (18-19) :1971-1979
[4]   BICYCLIC AND TRICYCLIC ERGOLINE PARTIAL STRUCTURES - RIGID 3-(2-AMINOETHYL)PYRROLES AND 3-(2-AMINOETHYL)PYRAZOLE AND 4-(2-AMINOETHYL)PYRAZOLE AS DOPAMINE AGONISTS [J].
BACH, NJ ;
KORNFELD, EC ;
JONES, ND ;
CHANEY, MO ;
DORMAN, DE ;
PASCHAL, JW ;
CLEMENS, JA ;
SMALSTIG, EB .
JOURNAL OF MEDICINAL CHEMISTRY, 1980, 23 (05) :481-491
[6]  
Bonnett R., 1981, ADV HETEROCYCL CHEM, V29, P341
[7]   SYNTHESIS OF SOME 3-HYDROXY-5-PYRIDYLPYRROLE DERIVATIVES [J].
CAMPAIGNE, E ;
SHUTSKE, GM ;
PAYNE, JC .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1977, 14 (02) :329-331
[8]   NEW HETEROCYCLIC RING-SYSTEMS .13. 7,11-DITHIAAZASTEROID ANALOGS [J].
CECCHETTI, V ;
FRAVOLINI, A ;
SCHIAFFELLA, F .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1982, 19 (05) :1045-1050
[9]   ENAMINO KETONES AS PRECURSORS OF FUNCTIONALIZED 2H-THIOPYRANS AND THIOPYRANO[2,3-C]BENZOTHIOPYRANS AND THIOPYRANO[3,2-B]BENZOTHIOPYRANS [J].
GABBUTT, CD ;
HEPWORTH, JD ;
HERON, BM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (20) :2603-2608
[10]  
GRIBBLE GW, 1996, COMPREHENSIVE HETERO, V2, P207, DOI DOI 10.1016/B978-008096518-5.00043-5