BIOMIMETIC SYNTHESIS OF PYRIDO[2,3,4-KL]ACRIDINES

被引:20
作者
GELLERMAN, G [1 ]
RUDI, A [1 ]
KASHMAN, Y [1 ]
机构
[1] TEL AVIV UNIV,SCH CHEM,IL-69978 TEL AVIV,ISRAEL
关键词
D O I
10.1016/S0040-4039(00)60789-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A short new biomimetic route to the pyrido[2,3,4-kl]acridine ring system has been developed from readily available benzoquinone, or hydroquinone precursors, and beta,beta'-diaminoketones like kynuramine (3) or 2,2'-diaminobenzophenone (4), involving one key step. Pyrido[2,3,4-kl]acridine and closely related compounds have been prepared (5-9). The reaction has been shown to proceed to the formation of 1:1 and/or 1:2 quinone/amine adducts. Using of o-aminoacetophenone afforded dibenzo[1,10]phenanthrolinedione (11) a potential intermediate to eilatin 2.
引用
收藏
页码:1823 / 1826
页数:4
相关论文
共 14 条
[1]   A SHORT NEW ROUTE TO THE PYRIDO[2,3,4-KL]ACRIDINE SUBUNIT COMMON TO PYRIDOACRIDINE ALKALOIDS OF MARINE ORIGIN [J].
ALI, NM ;
CHATTOPADHYAY, SK ;
MCKILLOP, A ;
PERRETGENTIL, RM ;
OZTURK, T ;
REBELO, RA .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (19) :1453-1454
[2]  
CARROLL AR, 1990, J ORG CHEM, V55, P4427
[3]   DIPLAMINE, A CYTO-TOXIC POLYAROMATIC ALKALOID FROM THE TUNICATE DIPLOSOMA SP [J].
CHARYULU, GA ;
MCKEE, TC ;
IRELAND, CM .
TETRAHEDRON LETTERS, 1989, 30 (32) :4201-4202
[4]   SHERMILAMINE-A - A PENTACYCLIC ALKALOID FROM A TUNICATE [J].
COORAY, NM ;
SCHEUER, PJ ;
PARKANYI, L ;
CLARDY, J .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (19) :4619-4620
[5]   SYNTHESIS OF PYRIDO[2,3,4-KL]ACRIDINES - A BUILDING BLOCK FOR THE SYNTHESIS OF PYRIDOACRIDINE ALKALOIDS [J].
GELLERMAN, G ;
RUDI, A ;
KASHMAN, Y .
TETRAHEDRON LETTERS, 1992, 33 (38) :5577-5580
[6]   DERCITIN, A NEW BIOLOGICALLY-ACTIVE ACRIDINE ALKALOID FROM A DEEP-WATER MARINE SPONGE, DERCITUS SP [J].
GUNAWARDANA, GP ;
KOHMOTO, S ;
GUNASEKERA, SP ;
MCCONNELL, OJ ;
KOEHN, FE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (14) :4856-4858
[7]   EUDISTONE-A AND EUDISTONE-B - 2 NOVEL OCTACYCLIC ALKALOIDS FROM A SEYCHELLES TUNICATE, EUDISTOMA SP [J].
HE, HY ;
FAULKNER, DJ .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (18) :5369-5371
[8]   VARAMINE-A AND VARAMINE-B, NEW CYTO-TOXIC THIOALKALOIDS FROM LISSOCLINUM-VAREAU [J].
MOLINSKI, TF ;
IRELAND, CM .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (17) :4256-4259
[9]   3,6-PHENANTHROLINES DERIVED FROM 2,2'-DIAMINOBENZOPHENONE [J].
PARTRIDGE, MW ;
VIPOND, HJ .
JOURNAL OF THE CHEMICAL SOCIETY, 1962, (FEB) :632-&
[10]   6 NEW ALKALOIDS FROM THE PURPLE RED-SEA TUNICATE EUDISTOMA SP [J].
RUDI, A ;
KASHMAN, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (22) :5331-5337