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Z. Naturforsch. 2014,
69b, 461 – 465
doi:10.5560/ZNB.2014-3276
Reactions of 2,2-Dialkyl-3-thioxochroman-4-one S-(1-Adamantylimides) with Some Nitrilimines
1 Current address: Chemistry Department, Faculty of Science & Arts, Qurayat, Al-Jouf University, Saudi Arabia
Permanent address: Photochemistry Department, National Research Centre, Dokki, 12622 Cairo, A. R. Egypt
2 Pesticides Chemistry Department, National Research Centre, Dokki, 12622 Cairo, A. R. Egypt
Reprint requests to Mohamed I. Hegab. E-mail:
pmihegab_2010@yahoo.com
Received October 5, 2013 / published online April 7, 2014
(E)-3-Thioxospiro[chroman-2,1′-cyclohexane]-4-one S-(1-adamantylimide) (1) reacted with numerous nitrilimines (generated in situ via triethylamine dehydrohalogenation of the corresponding hydrazonoyl chlorides 2a–i) in refluxing dry toluene to afford 3′′,5′′-disubstituted-3′′H,4′H-dispiro[cyclohexane-1,2′-chromene-3′,2′′-[1,3,4]thiadiazole]-4′-ones 3a–i. Similarly, reaction of 2,2-dimethyl-3-thioxochroman-4-one S-(1-adamantylimide) (4) with nitrilimines in refluxing dry toluene afforded the corresponding 3′,5′-disubstituted-3,3-dimethyl-3′H,4H-spiro[chromene-3,2′-[1,3,4]thiadiazole]-ones 5a–i.
Key words: Thioxo S-Imides, Nitrilimines, 1,3,4-Thiadiazole