Noncatalytic Annulation of 4-Hydroxy-4-methylpent-2-ynenitrile to 3,3-Dimethyl-2-phenyl-3 H -pyrrole. Stereoselective Synthesis of ( Z )-2-(2,2,7,7-Tetramethyl-7a-phenyl-7,7a-dihydropyrrolo- [2,1-b]oxazol-3(2 H )-ylidene)acetonitrile

L. A. Oparina; D. A. Shabalin; N. A. Kolyvanov; I. A. Ushakov; B. A. Trofimov

doi:10.1134/S1070428018120217

Noncatalytic Annulation of 4-Hydroxy-4-methylpent-2-ynenitrile to 3,3-Dimethyl-2-phenyl-3H-pyrrole. Stereoselective Synthesis of (Z)-2-(2,2,7,7-Tetramethyl-7a-phenyl-7,7a-dihydropyrrolo- [2,1-b]oxazol-3(2H)-ylidene)acetonitrile

Authors: Oparina L.A.¹, Shabalin D.A.¹, Kolyvanov N.A.¹, Ushakov I.A.¹, Trofimov B.A.¹
Affiliations:
1. Favorskii Irkutsk Institute of Chemistry, Siberian Branch
Issue: Vol 54, No 12 (2018)
Pages: 1848-1850
Section: Short Communications
URL: https://journals.rcsi.science/1070-4280/article/view/219608
DOI: https://doi.org/10.1134/S1070428018120217
ID: 219608

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Abstract

3,3-Dimethyl-2-phenyl-3H-pyrrole reacted with 4-hydroxy-4-methylpent-2-ynenitrile under mild conditions (20–25°C, 5 days) to give (Z)-2-(2,2,7,7-tetramethyl-7a-phenyl-7,7a-dihydropyrrolo[2,1-b]oxazol- 3(2H)-ylidene)acetonitrile in 79% yield with high stereoselectivity.