Selenolo pyrroles

Thieno- and Selenolo-pyrroles. Examples of these, e.g. (39 X = S or Se) and (40 X = S or Se), have been prepared by the reaction of ethyl azidoacetate with the monoaldehydes of thiophen or selenophen, followed by cyclization, hydrolysis, and decarboxylation of the product. ... 

Selenolo[3,2-6]pyrrole PE, 4, 1046 <77JOC2230> Selenolo[2,3-6]selenophene PE, 4, 1046 <77JOC2230) Selenolo[3,2-b]selenophene dipole moment, 4, 1049 (76AHC(19)123>... 

Selenolo[2,3-b]pyridine-2-carboxylic acid, 3-hydroxy-synthesis, 4, 1034 Selenolopyridines, 4, 1034—1036 H NMR, 4, 1035, 1036 Selenolo[2,3-c]pyridines synthesis, 4, 1035 Selenolo[3,2-b]pyridines deuteriodeprotonation, 4, 1035 synthesis, 4, 1034 Selenolo[3,2-c]pyridines synthesis, 4, 1035 Selenolo[2,3-b]pyrroles ionization potentials, 4, 1046 Selenolo[3,2-b]pyrroles ionization potentials, 4, 1046 Selenolo[3,4-c]pyrroles non-classical... 

Thieno[2,3-6 (thiophene Thieno[2,3-6 ]pyrrole Selenolo[2,3-6 (thiophene... 

Thieno[3,2- >]furan Thieno[3,2- >]pyrrole Selenolo[3,2-6]thiophene... 

Thicno[2,3-/ pyrrolyl)-l-alaninc 217 and 4-(6//-sclcnolo[2,3-/ pyrrolyl)-l-alanine 218, have been synthesized via reactions of thicnol 2,3-/ ]pyrrolc 215 and selenolo[2,3-fc]pyrrole 216, respectively, with 1-serine (Scheme 43). The reactions are catalyzed by Salmonella typhimurium tryptophan synthase [59,60],... 

Thieno[3,4-6]furan Thieno[2,3-c]pyrrole Selenolo[2,3-c]thiophene... 

Thieno[3,4-c]furan (37) Thieno[3,4-c]thiophene (38) Thiene[3,4-c]pyrrole (39) Selenolo[3,4-c]thiophene... 

Carbon-13 NMR parameters for 4//-thieno[3,2-6]pyrrole (9) and some other furo-, thieno-, and selenolo[3,2-6]pyrroles have been reported <76ACS(B)39i>. Carbon-13 chemical shifts and T(C,H) coupling constants of the 2-, 4-, and 6-substituted furo[3,2-6]pyrroles have been determined (Tables 6 and 7) <90MRC830>. The largest effect of a substituent attached at C-2 was observed on the C-2, C-3, and C-6a carbons. Additional 13C NMR data on furo[3,2-6]pyrrole derivatives have been reported <93CCC2139, 94MI 701-01). 

The l-methylbenzo 7>]furo-, benzo[ ]thieno-, and benzo[ ]selenolo[3,2- ]pyrroles (75), (76), and (77) were prepared <83JHC49> and the influence of annelation and of the heteroatom upon reactivity was tested toward acetylation and lithiation <83JHC6l>. The l-methylbenzo[ ]furo[3,2- ]pyrrole (75) was acetylated at C-2. 

The l-methylbenzo[A]thieno[2,3-/)]pyrrole (149) and benzo[6]selenolo[2,3-6]pyrrole (150) were prepared (83JHC49) and the influence of annelation and of the heteroatom upon the reactivity towards acetylation and lithiation was investigated <83JHC6l>. The sulfur and selenium analogues with [h,2-b (75)-(77) and [2,3-b (149) and (150) annelation were acetylated at C-2 and C-3. No reaction at all was observed with butyllithium except in the case of 1 -methylbenzo[6]selenolo[2,3-/ ]pyrrole (150), where the opening of the selenophene nucleus, after car-boxylation and the action of diazomethane, gave l-methyl-2-methoxycarbonyl-3-(2 -methyl-selenophenyl)pyrrole (151) and the positional isomer (152). 

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