Photochemical formation of novel pyrrolo[3,2-b]-6,7-benzobicyclo[3.2.1]octa-2,6-diene

被引:23
作者
Basaric, N [1 ]
Marinic, E [1 ]
Sindler-Kulyk, M [1 ]
机构
[1] Univ Zagreb, Fac Chem Engn & Technol, Dept Organ Chem, HR-10000 Zagreb, Croatia
关键词
D O I
10.1021/jo0346454
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first synthesis of 1,4,9,10-tetrahydro-4,9-methanobenzo[4,5]cyclohepta[1,2-b]pyrrole (11) was achieved by the photochemical intramolecular [2 + 2] cycloaddition of N-phenoxycarbonyl- (5a) and N-ethoxycarbonyl-2-[2-(2-vinylphenyl)]pyrrole (6a), respectively, followed by basic hydrolysis of the isolated N-substituted 1,4,9,10-tetrahydro-4,9-methanobenzo[4,5]cyclohepta[1,2-b]pyrroles (10a, 10b). Some competitively formed products were also isolated.
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页码:7524 / 7527
页数:4
相关论文
共 29 条
[1]   TRIPLET 1,4-BIRADICAL INTERMEDIATES IN THE PHOTOCYCLOADDITION REACTIONS OF ENONES AND N-ACYLINDOLES WITH ALKENES [J].
ANDREW, D ;
HASTINGS, DJ ;
OLDROYD, DL ;
RUDOLPH, A ;
WEEDON, AC ;
WONG, DF ;
ZHANG, B .
PURE AND APPLIED CHEMISTRY, 1992, 64 (09) :1327-1334
[2]  
Austin M, 1997, LIEBIGS ANN-RECL, P943
[3]   Structure elucidation of the photoproducts obtained by the photolysis of N-acetyl-2-styrylpyrroles [J].
Basaric, N ;
Ivekovic, D ;
Zimmermann, B ;
Marinic, E ;
Kowski, K ;
Rademacher, P ;
Sindler-Kulyk, M .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2003, 154 (2-3) :123-130
[4]   New photoinduced intramolecular ring closure to a benzopentaleno-pyrrole derivative from 5,5′-dimethyl-2,2′-(o-phenylenedivinylene)dipyrrole [J].
Basaric, N ;
Marinic, Z ;
Sindler-Kulyk, M .
TETRAHEDRON LETTERS, 2001, 42 (21) :3641-3643
[5]   Photochemical formation of indanylpyrrole derivatives from 2,2′-(o-phenylenedivinylene)dipyrrole [J].
Basaric, N ;
Tomsic, S ;
Marinic, Z ;
Sindler-Kulyk, M .
TETRAHEDRON, 2000, 56 (11) :1587-1593
[6]   Photochemical transformations of 2,2′-(1,2-phenylenedivinylene)-dipyrroles [J].
Basaric, Nikola ;
Marinic, Zeljko ;
Visnjevac, Aleksandar ;
Kojic-Prodic, Biserka ;
Griesbeck, Axel G. ;
Sindler-Kulyk, Marija .
PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, 2002, 1 (12) :1017-1023
[7]   1,4-PHOTOADDITION OF PYRROLE TO BENZENE [J].
BELLAS, M ;
BRYCESMI.D ;
GILBERT, A .
CHEMICAL COMMUNICATIONS, 1967, (06) :263-&
[8]  
BRUCESMITH D, 1971, CHEM COMMUN, P916
[9]   ORGANIC-PHOTOCHEMISTRY OF BENZENE .2. [J].
BRYCESMITH, D ;
GILBERT, A .
TETRAHEDRON, 1977, 33 (19) :2459-2490
[10]   Structure elucidation and assignment of 1H and 13C spectra of the new fused cyclobutane-naphthofuran derivative by two-dimensional NMR in different solvents [J].
Cvijin, IV ;
Marinic, Z ;
Sindler-Kulyk, M .
SPECTROSCOPY LETTERS, 1998, 31 (05) :989-1000