PubMed · 1207172
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G Cilento. 1975. Dioxetanes as intermediates in biological processes.. https://doi.org/10.1016/s0022-5193(75)80094-4
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Various thieno[3,4-b]indolizine derivatives having an acylmethylthio or (3-ethoxycarbonyl-2-propenyl)thio group at the 3-position which could not be obtained by a conventional method were prepared by a new procedure using cyanoethyl group as a protecting group and their intramolecular arene-pi interactions were investigated. In the (1)H-NMR spectra of these thieno[3,4-b]indolizines, the low-field shifts (delta 0.10-0.33 ppm) for the 5-protons were observed in comparison with those of 3-(methylthio)thieno[3,4-b]indolizines as a standard. The UV spectra also exhibited a characteristic absorption band at 425-445 nm attributable to the arene-pi interaction but their intensities were generally lower than those of 3-(arylmethylthio)thieno[3,4-b]indolizines. In their X-ray analyses, the anti conformation for 3-(acylmethylthio)thieno[3,4-b]indolizines and the gauche one for the 3-(3-ethoxycarbonyl-2-propenyl)thio derivatives were exhibited.
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[Structure: see text] A new method for direct phosphonation of thiazoles, furans, and pyrroles is introduced. Reactions of the heteroaryl compounds with dimethyl or diethyl phosphites and Mn(OAc)(3).2H2O under mild conditions give phosphonated products in high yield and good regioselectivity.