Literature DB >> 32100244

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

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

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.

Entities:  

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

Year:  2020        PMID： 32100244     DOI： 10.1007/s11030-020-10056-8

Source DB:  PubMed          Journal:  Mol Divers        ISSN： 1381-1991            Impact factor:   2.943


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  3 in total

1.  A synthesis of functionalized 3-amino-1,2,4-triazoles from nitrile imines and guanidine derivatives.

Authors:  Issa Yavari; Zohreh Taheri; Sara Sheikhi
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2.  A consecutive synthesis of spiro[cyclopenta[b]pyrrole-5,2'-indene] derivatives via spirocyclization/annulation reactions.

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Journal:  Mol Divers       Date:  2022-10-12       Impact factor: 3.364

3.  Reverse orientation in the ultrasound-assisted [3 + 2]-cycloaddition reaction of nitrile imines with 3-formylchromone-Meldrum's acid adducts.

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