HETEROCYCLIC COMPOUNDS WITH BRIDGEHEAD NITROGEN ATOMS .4. CYCLOPENTA [IJ]PYRIDO[2,1,6-DE]QUINOLIZINES (CYCLOPENTA[CD]CYCL[3,3,3]-AZINES)

被引:16
作者
CUNNINGHAM, RP
FARQUHAR, D
GIBSON, WK
LEAVER, D
机构
来源
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC | 1969年 / 02期
关键词
D O I
10.1039/j39690000239
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cyclopenta[c]quinolizines react with αβ-acetylenic esters to give cyclopenta[ij]pyrido[2,1,6-de]quinolizines (cyclopenta[cd]cycl[3,3,3]azines). The 1H n.m.r. spectra of the latter show evidence of aromatic character. Protonation of a dimethylcyclopentacyclazine occurred at the 1-position and treatment with benzoyl chloride gave a 1-benzoyl derivative. Other electrophilic reagents caused decomposition.
引用
收藏
页码:239 / +
页数:1
相关论文
共 19 条
[1]   AROMATIC MOLECULES BEARING SUBSTITUENTS WITHIN CAVITY OF PI-ELECTRON CLOUD . SYNTHESIS OF TRANS-15,16-DIMETHYLDIHYDROPYRENE [J].
BOEKELHE.V ;
PHILLIPS, JB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (07) :1695-&
[2]   FURTHER STUDIES ON 4-QUINOLIZONE DERIVATIVES [J].
BOEKELHEIDE, V ;
GALL, WG .
JOURNAL OF ORGANIC CHEMISTRY, 1954, 19 (04) :499-503
[3]   STUDY OF SOME SIMPLE QUINOLIZINIUM DERIVATIVES [J].
BOEKELHEIDE, V ;
KAEMPFEN, HX ;
FRITZ, H ;
ROSS, JM .
TETRAHEDRON, 1964, 20 (01) :33-&
[4]   DIHYDROPHYRIDINES FROM SILYLATION OF PYRIDINES [J].
COOK, NC ;
LYONS, JE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (14) :3396-&
[5]   STUDIES IN THE POLYENE SERIES .43. THE STRUCTURE AND SYNTHESIS OF VITAMIN-A2 AND RELATED COMPOUNDS [J].
FARRAR, KR ;
HAMLET, JC ;
HENBEST, HB ;
JONES, ERH .
JOURNAL OF THE CHEMICAL SOCIETY, 1952, (JUL) :2657-2668
[6]   1,5-DISUBSTITUTED ACENAPHTHENES - 5-MESITOYL-1-ACENAPHTHENEACETIC ACID [J].
FUSON, RC ;
FREY, SE .
JOURNAL OF ORGANIC CHEMISTRY, 1954, 19 (05) :810-816
[7]   SYNTHESIS OF A DERIVATIVE OF CYCL[3,3,3]AZINE (9B-AZAPHENALENE) [J].
GIBSON, WK ;
LEAVER, D .
CHEMICAL COMMUNICATIONS, 1965, (01) :11-&
[8]   HETEROCYCLIC COMPOUNDS WITH BRIDGEHEAD NITROGEN ATOMS .3. FORMATION OF CYCLOPENTA[C]QUINOLIZINES FROM 3-ALPHA-DIMETHYL-AMINOVINYLINDOLIZINES AND DIMETHYL ACETYLENEDICARBOXYLATE [J].
GIBSON, WK ;
LEAVER, D .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1966, (03) :324-&
[9]   SYNTHESIS OF SEVERAL 4,6-DIMETHYLQUINOLIZINIUM SALTS, POSSIBLE PRECURSORS OF CYCL[3.3.3]AZINE [J].
HANSEN, HV ;
AMSTUTZ, ED .
JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (02) :393-&
[10]   STUDIES IN NUCLEAR MAGNETIC RESONANCE .3. ASSIGNMENT OF CONFIGURATIONS OF ALPHA,BETA-UNSATURATED ESTERS AND THE ISOLATION OF PURE TRANS-BETA-METHYLGLUTACONIC ACID [J].
JACKMAN, LM ;
WILEY, RH .
JOURNAL OF THE CHEMICAL SOCIETY, 1960, (JUL) :2886-2890