Synthetic studies on pyrrolophenanthridone skeleton from 1-benzoyl-7-iododihydroindole derivatives using palladium-assisted biaryl coupling reactions

被引:12
作者
Harayama, T [1 ]
Toko, H [1 ]
Hori, A [1 ]
Miyagoe, T [1 ]
Sato, T [1 ]
Nishioka, H [1 ]
Abe, H [1 ]
Takeuchi, Y [1 ]
机构
[1] Okayama Univ, Fac Pharmaceut Sci, Okayama 7008530, Japan
关键词
C-H activation; regioselectivity; anhydrolycorin-7-one; oxoassoanine;
D O I
10.3987/COM-03-S10
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The biaryl coupling reaction of 1-benzoyl-7-iododihydroindole derivatives using Pd reagent was examined. 1-[(1,3-Benzodioxol-5-yl)carbonyl]-7-iodo-2,3-dihydroindole gave 4,5-dihydro-7H-[1,3]dioxolo[4,5-k]pyrrolo[3,2,1-de]phenanthridin-7-one, which was formed by connection to a more hindered carbon, as a major product. 1-(3,4-Dimethoxybenzoyl)-7-iodo-2,3-dihydroindole gave oxoassoanine and 10,11-dimethoxy-4,5-dihydropyrrolo[3,2,1-de]phenanthridin-7-one in an almost equal ratio.
引用
收藏
页码:513 / +
页数:9
相关论文
共 24 条
[1]   SYNTHESIS OF PYRROLOPHENANTHRIDONES BY ARYL-ARYL COUPLING REACTIONS [J].
BLACK, DS ;
KELLER, PA ;
KUMAR, N .
TETRAHEDRON, 1993, 49 (01) :151-164
[2]   PHOTOLYSIS OF 1-BENZOYL-INDOLE AND 1-ORTHO-IODOBENZOYL-INDOLE AND 3-ORTHO-LODOBENZOYL-INDOLE [J].
CARRUTHERS, W ;
EVANS, N .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (13) :1523-1525
[3]   CHEMICAL-CONSTITUENTS OF AMARYLLIDACEAE .4. EFFECTS OF HIPPADINE, AN AMARYLLIDACEAE ALKALOID, ON TESTICULAR FUNCTION IN RATS [J].
CHATTOPADHYAY, S ;
CHATTOPADHYAY, U ;
MATHUR, PP ;
SAINI, KS ;
GHOSAL, S .
PLANTA MEDICA, 1983, 49 (04) :252-254
[4]   MICROBIOLOGICAL TRANSFORMATIONS .6. MICROBIOLOGICAL TRANSFORMATIONS OF ACYL DERIVATIVES OF INDOLINE, 1,2,3,4-TETRAHYDROQUINOLINE, 1,2,3,4-TETRAHYDROISOQUINOLINE AND "2,3,4,5-TETRAHYDRO-1H-1-BENZAZEPINE WITH THE FUNGUS CUNNINGHAMELLA-ELEGANS [J].
CRABB, TA ;
SOILLEUX, SL .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (07) :1381-1385
[5]   An investigation of a palladium catalysed biaryl synthesis of pyrrolophenanthridine derivatives. Extension of the Heck reaction. [J].
Garden, SJ ;
Torres, JC ;
Pinto, AC .
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2000, 11 (05) :441-446
[6]   CHEMICAL-CONSTITUENTS OF AMARYLLIDACEAE .1. ALKALOIDS OF CRINUM-PRATENSE [J].
GHOSAL, S ;
RAO, PH ;
JAISWAL, DK ;
KUMAR, Y ;
FRAHM, AW .
PHYTOCHEMISTRY, 1981, 20 (08) :2003-2007
[7]   Concise synthesis of nitidine by palladium-assisted biaryl coupling reaction [J].
Harayama, T ;
Shibaike, K .
HETEROCYCLES, 1998, 49 :191-195
[8]   Concise synthesis of fagaridine and decarine, phenolic benzo[c]phenanthridine alkaloids, using the palladium-assisted biaryl coupling reaction [J].
Harayama, T ;
Sato, T ;
Nakano, Y ;
Abe, H ;
Takeuchi, Y .
HETEROCYCLES, 2003, 59 (01) :293-301
[9]   Aryl-aryl coupling reaction using a novel and highly active palladium reagent prepared from Pd(OAc)2, 1,3-bis [diphenylphosphino]propane (DPPP), and Bu3P [J].
Harayama, T ;
Akiyama, T ;
Nakano, Y ;
Nishioka, H ;
Abe, H ;
Takeuchi, Y .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2002, 50 (04) :519-522
[10]   Aryl-aryl coupling reaction catalyzed by a palladium reagent prepared from Pd(OAc)2 and n-Bu3P [J].
Harayama, T ;
Hori, A ;
Nakano, Y ;
Akiyama, T ;
Abe, H ;
Takeuchi, Y .
HETEROCYCLES, 2002, 58 :159-164