The synthesis of sydnones heteroarylated at C-4 with an indolizine was achieved by Chichibabin (Tschitschibabin) indolizine synthesis starting from the corresponding sydnone-N-pyridinium bromides. The latter compounds were also transformed to sydnone-indolizines connected through a keto group at the C-4 position by refluxing them in 1,2-epoxybutane with an activated alkyne. The structures of th...

Ultrasound irradiation can promote the 1,3-dipolar cycloaddition reaction of 2-chloropyridinium ylides with 2-benzylidenemalononitrile or 2,2'-(1,4-phenylenebis(methanylylidene))dimalononitrile, to afford the indolizine and bis-indolizine derivatives respectively. While the reaction of pyridinium ylides with 2-benzylidenemalononitrile or 2,2'-(1,4-phenylenebis(methanylylidene))dimalononitrile u...

Five new spiro[indoline-3,3′-indolizine]s have been synthesized with high regio- and stereospecificity in one-pot three-component reactions between a substituted indole-2,3-dione, ( S )-pipecolic acid trans -3-benzoylacrylic acid, subsequently characterized using combination of elemental analysis, IR 1 H 13 C NMR spectroscopy, mass spectrometry crystal structure analysis. (1′ SR ,2′ ,3 RS ,8a′ ...

Several heterocyclic bioactive fluorescent 3-alkyl-3H-pyrazolo[4,3-a]acridin-11-carbonitriles were conveniently synthesized from the reaction of 1-alkyl-1H-indazoles with different aryl acetonitrile in basic methanol solution in good yields. The interactions of 3H-pyrazolo[4,...

In the title E isomer of the racemic compound, C37H32F2N2O2, the pyridinone ring adopts a twisted half-chair conformation with the N atom deviating by -0.355 (3) Å and with the methyl-ene C atom next to octa-hydro-indolizine moiety deviating by 0.415 (3) Å from the mean plane defined by other four atoms. In the octa-hydro-indolizine system, the pyrrolidine ring exhibits an envelope conformation...

In the title compound, C(10)H(15)NO(3), the central six-membered ring of the indolizine system adopts a chair conformation, while the oxopyrrolidine and hydro-furan rings attached to the indolizine ring system have envelope conformations. In the crystal, the mol-ecules form chains parallel to the b axis via inter-molecular O-H⋯O hydrogen bonds. The absolute configuration was assigned from the s...

In the mol-ecular structure of the title compound, C(14)H(21)NO(5), the six-membered ring of the indolizine moiety adopts a chair conformation. There are two independent mol-ecules in the asymmetric unit. The oxopyrrolidine ring attached to the indolizine ring system is nearly planar, with mean deviations of 0.018 (3) and 0.010 (3) Å for the two mol-ecules. The absolute configuration of the tit...

In the title compound, C(39)H(38)N(2)O(4), the pyridinone ring adopts a twisted half-chair conformation with the N atom deviating by 0.3304 (1) and with the methyl-ene C atom adjacent to the octa-hydro-indolizine unit deviating by 0.444 (3) Å from the mean plane defined by the other four atoms. In the octa-hydro-indolizine system, the pyrrolidine ring exhibits an envelope conformation, with the...

Carbonitriles and alcohols react in a Lewis acid-promoted Pinner reaction to carboxylic esters. Best results are obtained with two equivalents of trimethylsilyl triflate as Lewis acid. Good yields are achieved with primary alcohols and aliphatic or benzylic carbonitriles, but the straightforward synthesis of acrylates and benzoates starting with acrylonitrile and benzonitrile, respectively, is ...