40566-13-0Relevant academic research and scientific papers
Pd-catalyzed chemoselective catellani orth -arylation of iodopyrroles: Rapid total synthesis of rhazinal
Sui, Xianwei,Zhu, Rui,Li, Gencheng,Ma, Xinna,Gu, Zhenhua
supporting information, p. 9318 - 9321 (2013/07/25)
A Pd-catalyzed chemoselective Catellani reaction of iodopyrroles was developed. The rare chemoselectivity between two different aryl halides was realized by optimizing the kinetics of the different steps of this multicomponent process. The new developed method led to the rapid synthesis of rhazinal in a highly efficient manner.
Total synthesis of (±)-rhazinal using novel palladium-catalyzed cyclizations
Bowie, Alfred L.,Trauner, Dirk
experimental part, p. 1581 - 1586 (2009/07/17)
A concise synthesis of (±)-rhazinal that hinges on novel oxidative Heck cyclizations and palladium- catalyzed direct couplings is described. An X-ray structure of N-MOM-rhazinal, which provides insight into the conformation of the strained 9-membered lact
A short synthesis of a thienyl analogue of undecylprodigiosin
D'Auria, Maurizio,De Luca, Eliana,Mauriello, Giacomo,Racioppi, Rocco
, p. 35 - 42 (2007/10/03)
The photochemical coupling between 4,5-diiodopyrrole-2-carbaldehyde and thiophene gave 4-iodo-5-(2-thienyl)pyrrole-2-carbaldehyde. Dehalogenation reaction and the coupling of the product with undecylpyrrole gave an analogue of undecylprodigiosin, an immunosuppressive drug.
Photochemical substitution of halogenopyrrole derivatives
D'Auria, Maurizio,De Luca, Eliana,Mauriello, Giacomo,Racioppi, Rocco,Sleiter, Giancarlo
, p. 2369 - 2373 (2007/10/03)
The photochemical behaviour of some iodo substituted pyrroles when they are irradiated in the presence of an aromatic compound is reported. N-Methyl-3,4-diiodopyrrole-2-carbaldehyde and 5-iodopyrrole-2-carbaldehyde are unreactive when they are irradiated in benzene solution. In contrast, ethyl 3,4-dimethyl-5-iodopyrrole-2-carboxylate gives a 1:1 mixture of ethyl 3,4-dimethyl-5-phenylpyrrole-2-carboxylate and ethyl 3,4-dimethylpyrrole-2-carboxylate in quantitative yields. The same reaction when attempted with acetonitrile as solvent gives ethyl 3,4-dimethylpyrrole-2-carboxylate as the sole product in quantitative yield. Use of 4,5-diiodopyrrole-2-carbaldehyde as substrate and irradiation in benzene gives the corresponding 5-phenyl derivative. The same behaviour is observed with m-xylene, thiophene and 2-chlorothiophene as solvents. With acetonitrile as solvent, the reaction with benzene does not work. With 2-methylthiophene as solvent 2-(5-methyl-2-thienyl)-3-iodopyrrole is obtained as the sole product. The observed behaviour can be explained on the basis of the previously reported data on the mechanism of the photochemical arylation of halogenothiophene derivatives.
