PHOTOCYCLIZATION OF ENAMIDES .13. SUBSTITUENT EFFECTS IN THE PHOTOCYCLIZATION OF N-BENZOYLENAMINES

被引：20

作者：

NINOMIYA, I

KIGUCHI, T

YAMAMOTO, O

NAITO, T

机构：

[1] Kobe Women's College of Pharmacy, Motoyamakita, Higashinada

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1979年 / 07期

关键词：

D O I：

10.1039/p19790001723

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

trans-Hexahydrophenanthridones (IIa-g) and trans-tetrahydrobenzo[c] phenanthridones (VIa-e) were prepared by stereospecific photocyclisation of a variety of N-benzoylenamines (Ia-n) and (Va-g) bearing either electron-donating or -attracting substituents on the benzoyl group. Suprafacial [1,5] migration of an o-methoxy-group upon cyclisation and photoinduced trans-cis-isomerisation of some benzo[c]phenanthridones (VIa-c) were observed.

引用

收藏

页码：1723 / 1728

页数：6

相关论文

共 14 条

[1] ANNELATED FURANS .18. PHOTOCYCLIZATION OF 2-METHOXYPHENYL PHENYL ETHERS [J].

ELIX, JA ;

MURPHY, DP .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1975, 28 (07) :1559-1582

[2] PHOTOCHEMICAL-SYNTHESIS OF PHENANTHRENES FROM 2-METHOXYSTILBENES [J].

GILES, RGF ;

SARGENT, MV .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (21) :2447-2450

[3]

ISHII H, 1978, CHEM PHARM BULL, V26, P864

[4]

JOSHUA CP, 1973, TETRAHEDRON LETT, P3559

[5] STUDIES ON SYNTHESIS OF HETEROCYCLIC-COMPOUNDS .698. ALTERNATIVE PROTOBERBERINE SYNTHESIS - TOTAL SYNTHESIS OF (+1-)-XYLOPININE, (+1-)-SCHEFFERINE, (+1-)-NANDININE, (+1-)-CORYDALINE, AND (+1-)-THALICTRICAVINE [J].

KAMETANI, T ;

SUGAI, T ;

SHOJI, Y ;

HONDA, T ;

SATOH, F ;

FUKUMOTO, K .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (10) :1151-1155

[6] PHOTOCYCLIZATION OF BENZANILIDES TO PHENANTHRIDONES WITH ELIMINATION OF ORTHO-METHOXY GROUP [J].

KANAOKA, Y ;

ITOH, K .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1973, (18) :647-648

[7] ENAMIDE PHOTOCHEMISTRY - FORMATION OF 8-OXOBERBINES FROM 2-AROYL-1-METHYLENE-1,2,3,4-TETRAHYDROISOQUINOLINES [J].

LENZ, GR .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (19) :2846-2851

[8] ENAMIDE PHOTOCHEMISTRY - FORMATION OF OXYPROTOBERBERINES BY ELIMINATION OF ORTHO SUBSTITUENTS IN 2-AROYL-1-METHYLENE-1,2,3,4-TETRAHYDROISOQUINOLINES [J].

LENZ, GR .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (19) :2839-2845

[9] PHOTOCYCLIZATION OF ENAMIDES .3. PHOTOCYCLIZATION OF N-BENZOYLENAMINES OF CYCLOHEXANONE AND 2-SUBSTITUTED CYCLOHEXANONES [J].

NINOMIYA, I ;

NAITO, T ;

KIGUCHI, T .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (20) :2257-2261

[10]

NINOMIYA I, 1974, J CHEM SOC CHEM COMM, P81, DOI 10.1039/c39740000081