SYNTHESIS OF SOME HYDROXYMETHYL-AND AMINOMETHYL-INDOLIZINES

被引:28
作者
JONES, G
STANYER, J
机构
[1] Chemistry Department, University of Keele, Keele
来源
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC | 1969年 / 06期
关键词
D O I
10.1039/j39690000901
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Syntheses are reported of 2-hydroxymethylindolizine (4), 3-hydroxymethylindolizine (5), and 2-methyl-6-hydroxymethylindolizine (6). Attempts to prepare 1-hydroxymethyl-2-methylindolizine by reduction of the corresponding ethoxycarbonyl derivative or by a Chichibabin synthesis from a 2-pyridylethanol derivative were unsuccessful, although 1-(2-hydroxyethyl)-2- methylindolizine (13) was so obtained. The very unstable 2-aminomethylindolizine (15) and 7-aminomethyl-2-methylindolizine (34) have been obtained by reduction of the corresponding nitrites; attempts to obtain 6-aminomethyl-2- methylindolizine are described.
引用
收藏
页码:901 / &
相关论文
共 13 条
[1]   ADDITION REACTIONS OF HETEROCYCLIC COMPOUNDS .38. CYCL-[3,2,2]AZINES AND INDOLIZINES FROM PYRIDINES AND METHYL PROPIOLATE [J].
ACHESON, RM ;
ROBINSON, DA .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (13) :1633-&
[2]   THE CHEMISTRY OF THE PYRROCOLINES .6. THE SYNTHESIS OF PYRROCOLINE-2-CARBOXYLIC ACID - A NEW ROUTE TO PYRROCOLINE [J].
BORROWS, ET ;
HOLLAND, DO .
JOURNAL OF THE CHEMICAL SOCIETY, 1947, (MAY) :672-674
[3]   THE CHEMISTRY OF THE PYRROCOLINES .5. THE ACTION OF GRIGNARD REAGENTS AND OF IODINE ON 3-ACETYL-2-PHENYLPYRROCOLINE [J].
BORROWS, ET ;
HOLLAND, DO .
JOURNAL OF THE CHEMICAL SOCIETY, 1947, (MAY) :670-672
[4]   PREPARATION OF INDOLIZINES FROM ETHYL 2-PYRIDYLACETATE [J].
BRAGG, DR ;
WIBBERLEY, DG .
JOURNAL OF THE CHEMICAL SOCIETY, 1962, (JUL) :2627-&
[5]   CYANATION OF AMINE OXIDE SALTS - A NEW SYNTHESIS OF CYANOPYRIDINES [J].
FEELY, WE ;
BEAVERS, EM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (15) :4004-4007
[6]   THE CHEMISTRY OF THE PYRROCOLINES .7. FURTHER EXPERIMENTS WITH 2-METHYLPYRROCOLINE [J].
HOLLAND, DO ;
NAYLER, JHC .
JOURNAL OF THE CHEMICAL SOCIETY, 1955, :1504-1511
[7]   THE CHEMISTRY OF THE PYRROCOLINES .8. ALKYL DERIVATIVES [J].
HOLLAND, DO ;
NAYLER, JHC .
JOURNAL OF THE CHEMICAL SOCIETY, 1955, :1657-1662
[8]   INDOLIZINES .3. [J].
HURST, J ;
MELTON, T ;
WIBBERLEY, DG .
JOURNAL OF THE CHEMICAL SOCIETY, 1965, (APR) :2948-+
[9]   INDOLIZINES .4. SYNTHESES FROM 2-ACYLMETHYLENE-1-BENZYL-1,2-DIHYDROPYRIDINE PHENYL-2-PICOLYL SULPHONE AND RELATED COMPOUNDS [J].
MELTON, T ;
WIBBERLE.DG .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (10) :983-&
[10]  
Okamoto T., 1959, CHEM PHARM BULL, V7, P130