138905-53-0Relevant academic research and scientific papers
Photochemical synthesis of pyrrole derivatives by desulfurization of 2,5-dihydro-1H-pyrrole-2-thiones and [2 + 2] cycloaddition of 2,5-dihydro-1H-pyrrole-2-thiones with alkenes
Nishio, Takehiko
, p. 885 - 889 (2007/10/03)
The photochemical reactions of the 2,5-dihydro-1H-pyrrole-2-thiones 2 have been examined. Irradiation of 2,5-dihydro-1H-pyrrole-2-thiones 2 in the presence of triethylamine gives desulfurization products, the pyrroles 3, or reduction products, the pyrrolidine-2-thiones 4, depending on the substituent on the nitrogen atom of thione 2. This reaction can be explained by a sequential electron/proton-transfer mechanism from the amine to the excited pyrrolethione. Irradiation of thiones 2 in the presence of alkenes 5 gives 2-alkylated pyrroles 6-14. The formation of these photoproducts can be explained in terms of the intermediacy of spiroaminothietanes, which are derived by [2 + 2] photocycloaddition of the C=S bond of thione 2 and the C=C bond of alkene 5.
Novel Route to 4,5,6,7-Tetrahydroindoles and Pyrroles
Nishio, Takehiko,Okuda, Norikazu,Kashima, Choji
, p. 899 - 902 (2007/10/02)
Treatment of cyclic unsaturated amides, 1,4,5,6,7,7a-hexahydro-2H-indol-2-ones 1, with Lawesson's reagent yielded unexpected products, 4,5,6,7-tetrahydroindoles 2, in moderate yield.Re
3-Hydroxypyrroles and 1H-Pyrrol-3(2H)-ones. Part 10. Alkylation of Pyrrolones under Basic Conditions: Regiospecific Formation of 3-Alkoxypyrroles
Hunter, Gordon A.,McNab, Hamish,Monahan, Lilian C.,Blake, Alexander J.
, p. 3245 - 3251 (2007/10/02)
Alkylation of 1-substituted 1H-pyrrol-3(2H)-ones 1 in the presence of base generally gives a mixture of O-alkylated 3, C,O-dialkylated 4 and C,C-dialkylated 5 products.The proportion of C-alkylation is increased by the use of a soft alkylating agent (e.g. iodomethane) and a solvent of l ow polarity (e.g.THF), whereas O-alkylation is favoured by hard alkylating agents (e.g. methyl toluene-p-sulphonate), and dipolar aprotic solvents (e.g. dimethylimidazolidinone).These latter conditions give a good preparative route to a wide range of 1-substituted and 1,2-disubstituted 3-alkoxypyrroles 3 (65-90percent yield).The X-ray crystal structure of 1-tert-butyl-3-methoxy-2-phenylpyrrole 22 is reported.
