New transition metal-catalyzed methods for the arylation of indolizines by the direct cleavage of C-H bonds have been developed. A wide range of aryltrifluoroborate salts react with indolizines in the presence of Pd(OAc)(2) catalyst and AgOAc oxidant to give the arylated indolizines in high yields. Both electron-donating and electron-withdrawing groups perform smoothly while bromide and chlorin...

Post-functionalization at the C3 position of indolizines via In(iii)-catalyzed three-component coupling reaction with amines and aldehydes allowed rapid access to a new class of indolizines with diverse functional groups at the C3 position in good to excellent yields.

Divergent syntheses of indolizines and 2,4-disubstituted pyrroles by the silver-catalyzed cyclization of 2-pyridyl alkynyl carbinols with isocyanides are reported. These methods provide an effective route to highly functionalized indolizines and 2,4-disubstituted pyrroles in good to excellent yields. The 2,4-disubstituted pyrroles are synthesized by an unprecedented regioselective [3+2] cycload...

A direct and regioselective C1-acyloxylation of indolizines was developed via palladium-catalyzed C-H functionalization. A series of indolizines were successfully acyloxylated at the C1 position with the tolerance of a broad range of functional groups. In this reaction, high regioselectivity was achieved in the absence of a directing group. This work represents the first example of indolizine a...

A novel method for the C-C bond cleavage of cyclopropanes was developed by gold-catalyzed cycloisomerization of 2-(1-alkynyl-cyclopropyl)pyridine with nucleophiles, which provides efficient access to structurally diverse indolizines under mild conditions. A series of N-, C- and O-based nucleophiles were involved in this reaction to afford the corresponding indolizines in modest to excellent yie...

The three possible structural isomers of 4-(pyridyl)pyrimidine were employed for the synthesis of new pyrrolo[1,2-c]pyrimidines and new indolizines, by 1,3-dipolar cycloaddition reaction of their corresponding N-ylides generated in situ from their corresponding cycloimmonium bromides. In the case of 4-(3-pyridyl)pyrimidine and 4-(4-pyridyl)pyrimidine the quaternization reactions occur as expect...

Various 2-substituted indolizines can be directly and selectively lithiated in the 5 position and subsequent reactions with different electrophiles lead to some novel classes of indolizines. In particular, previously unknown 5-formyl- and 5-iodoindolizine have been prepared by this way and the molecular structure of 5-formyl-2- phenylindolizine was confirmed by X-Ray analysis. The reactivity of...

The absolute configuration of the title compound, C14H13NO3S, was assigned from the synthesis and confirmed by the structure determination. The central six-membered ring of the indolizine moiety adopts an envelope conformation, with the greatest deviation from the mean plane of the ring being 0.661 (2) Å for the bridgehead C atom. The benzothiene ring attached to the indolizine ring system is p...

Various 2-substituted indolizines can be directly and selectively lithiated in the 5 position and subsequent reactions with different electrophiles lead to some novel classes of indolizines. In particular, previously unknown 5-formyland 5-iodoindolizine have been prepared by this way and the molecular structure of 5-formyl-2phenylindolizine was confirmed by X-Ray analysis. The reactivity of the...

An efficient approach to the synthesis of 1,2,3-trisubstituted indolizines is described via one-pot reactions of pyridine and dialkyl acetylendicarboxylate in the presence of ethyl 2-chloroacetoacetate in MeOH at room temperature. The corresponding 1, 2, 3-trisubstituted indolizines may be useful building blocks for the construction of complex indolizine derivatives.