Synthesis and reactions of heterocyclic 2,3‐epoxypropionitriles with pyrrolidine | Zendy

Agarwal Kamlesh C. | Zendy; Knaus Edward E. | Zendy

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Synthesis and reactions of heterocyclic 2,3‐epoxypropionitriles with pyrrolidine

Author(s) -

Agarwal Kamlesh C.,

Knaus Edward E.

Publication year - 1987

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570240103

Subject(s) - chemistry , pyrrolidine , propionitrile , yield (engineering) , acrylonitrile , stereochemistry , medicinal chemistry , organic chemistry , acetonitrile , materials science , copolymer , metallurgy , polymer

The Darzen's reaction of 2‐(3‐)pyridinecarboxaldehydes 5 with chloroacetonitrile yielded a mixture of stereoisomers cis ‐ 6 and trans ‐3‐(pyridinyl)‐2,3‐epoxypropionitriles 7 in a ratio of approximately 1:1. Oxidation of cis ‐ 6 and trans ‐ 7 afforded the corresponding cis ‐ 8 and trans ‐3‐(1‐oxidopyridinyl)‐2,3‐epoxypropionitriles 9 in good yield. The reaction of 8a and 9a with pyrrolidine at 25° gave the respective threo ‐ 10 and erthyro‐2 ‐(1‐pyrrolidino)‐3‐hydroxy‐3‐(1‐oxido‐2‐pyridinyl)propionitrile ( 11 ). A number of selected compounds ( 7‐9a‐b ) were found to be inactive in the P388 Lymphocyctic screen.

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