Synthesis of spiro pyrrolidines via formal [3+2] cycloaddition of unusual enones and cis-3-benzoyl-1-cyclohexyl-2-phenylaziridine

Raj, A. Amal; Raghunathan, R.

doi:10.1016/s0040-4020(03)00346-6

Cited by 15 publications

(1 citation statement)

References 19 publications

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“…For background to the synthesis, see: Amalraj & Raghunathan (2003). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).…”

Section: Related Literaturementioning

confidence: 99%

4′-(4-Chlorophenyl)-1′-methyldispiro[indan-2,2′-pyrrolidine-3′,2′′-indan]-1,3,1′′-trione

Wei¹,

Ali²,

Yoon³

et al. 2011

Acta Cryst E

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In the title compound, C27H20ClNO3, the two cyclopentane rings adopt envelope conformations. The pyrrolidine ring also adopts an envelope conformation (with the spiro C atom as the flap) and its least-squares plane (fitted to five atoms) makes dihedral angles of 66.50 (9), 77.36 (8) and 73.76 (8)° with the chlorobenzene ring and the two 2,3-dihydro-1H-indene ring systems, respectively. The molecular conformation is stabilized by an intramolecular C—H⋯O hydrogen bond, which generates an S(6) ring motif. In the crystal, molecules are linked by C—H⋯O hydrogen bonds into chains running parallel to the [001] direction.

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“…For background to the synthesis, see: Amalraj & Raghunathan (2003). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).…”

Section: Related Literaturementioning

confidence: 99%

4′-(4-Chlorophenyl)-1′-methyldispiro[indan-2,2′-pyrrolidine-3′,2′′-indan]-1,3,1′′-trione

Wei¹,

Ali²,

Yoon³

et al. 2011

Acta Cryst E

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Theoretical Studies on Cycloaddition Reactions between 1‐Aza‐2‐azoniaallene Cations and Isocyanates

Wei¹,

Fang²,

Liu³

2004

Eur J Org Chem

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The mechanisms of the title reactions between 1‐aza‐2‐azoniaallene cations and isocyanic acid or isocyanates have been theoretically explored at the B3LYP/6‐31++G** level. It was found that all of these reactions proceed in asynchronous but concerted pathways. The substituent effects are also obvious; e.g., the presence either of an electron‐withdrawing chlorine substituent on the 1‐aza‐2‐azoniaallene cation or of an electron‐releasing methyl substituent on the isocyanate both favor the cycloaddition reactions. For the [1,2]‐shift reactions, all the substituents lower their activation barrier, especially Cl substituents on the 1‐aza‐2‐azoniaallene cation, but when Cl substituents are present on the 1‐aza‐2‐azoniaallene cation the rearrangement product is not as stable as others. In addition, solvent effects with the PCM model are also reported, and a model reaction has been investigated at the MP2/6‐31+G* and QCISD/6‐31+G* levels as well as by DFT. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

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One pot synthesis of novel dispiro[oxindole‐thiazolidinedione/thioxo‐thiazolidinone/dihydro pyrazolone]‐pyrrolidines via 1,3‐dipolar cycloaddition reaction of azomethine ylides

Ponnala

Sahu

Kumar

et al. 2006

Journal of Heterocyclic Chem

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A series of novel dispiro [oxindole-thiazolidinedione]pyrrolidine, dispiro[oxindole-thioxothiazolidinone]-pyrrolidine, dispiro[oxindole-dihydro-pyrazolone]pyrrolidine were synthesized by both regio-and stereoselective 1,3-dipolar cycloaddition reaction of azomethine ylide generated from amino acid and amino acid ester with -deficient alkenes in a single pot protocol in good yield. X-ray crystallographic studies established orthogonal disposition between spiro-oxindole and spiro -thiazolidinedione rings in 4a and 5a.

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Synthesis of spiro pyrrolidines via formal [3+2] cycloaddition of unusual enones and cis-3-benzoyl-1-cyclohexyl-2-phenylaziridine

Cited by 15 publications

References 19 publications

4′-(4-Chlorophenyl)-1′-methyldispiro[indan-2,2′-pyrrolidine-3′,2′′-indan]-1,3,1′′-trione

4′-(4-Chlorophenyl)-1′-methyldispiro[indan-2,2′-pyrrolidine-3′,2′′-indan]-1,3,1′′-trione

Theoretical Studies on Cycloaddition Reactions between 1‐Aza‐2‐azoniaallene Cations and Isocyanates

One pot synthesis of novel dispiro[oxindole‐thiazolidinedione/thioxo‐thiazolidinone/dihydro pyrazolone]‐pyrrolidines via 1,3‐dipolar cycloaddition reaction of azomethine ylides

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