Synthesis of thia- and thioxo-tetraazaspiro[4.4]nonenones from nitrile imines and arylidenethiohydantoins

Issa Yavari; Zohreh Taheri; Sara Sheikhi; Samira Bahemmat; Mohammad R Halvagar

doi:10.1007/s11030-020-10056-8

Synthesis of thia- and thioxo-tetraazaspiro[4.4]nonenones from nitrile imines and arylidenethiohydantoins

Mol Divers. 2021 May;25(2):777-785. doi: 10.1007/s11030-020-10056-8. Epub 2020 Feb 25.

Authors

Issa Yavari¹, Zohreh Taheri², Sara Sheikhi², Samira Bahemmat³, Mohammad R Halvagar³

Affiliations

¹ Department of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Iran. yavarisa@modares.ac.ir.
² Department of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Iran.
³ Department of Inorganic Chemistry, Chemistry and Chemical Engineering Research Center of Iran, P.O. Box 14335-186, Tehran, Iran.

PMID: 32100244
DOI: 10.1007/s11030-020-10056-8

Abstract

5-Arylidene-1-methyl-2-thiohydantoins undergo [3+2]-cycloaddition reaction with nitrile imines, generated in situ from hydrazonyl chlorides, at C=C and C=S dipolarophiles in the thiohydantoin moiety to afford thioxo-tetraazaspiro[4.4]nonenones and thia-tetraazaspiro[4.4]nonenones in moderate to good yields. The stereochemistry of these spiroheterocycles has been confirmed by X-ray diffraction studies.

Keywords: 1,3-Dipolar cycloaddition; Nitrile imines; Spirocycles; Tetraazaspiro[4.4]nonenones; Thiohydantoins.

MeSH terms

Cycloaddition Reaction
Hydantoins / chemistry*
Imines / chemistry*
Nitriles / chemistry*
Spiro Compounds / chemical synthesis*
Spiro Compounds / chemistry

Substances

Hydantoins
Imines
Nitriles
Spiro Compounds