Reactions of fused dihydro-1,2,4-thiadiazoles with isocyanates and isothiocyanates to give 6aλ4-thia-1,3,4,6-tetraazapentalene derivatives
✍ Scribed by Long-Li Lai; David H. Reid; Robin H. Nicol; Jane B. Rhodes
- Publisher
- John Wiley and Sons
- Year
- 1994
- Tongue
- English
- Weight
- 710 KB
- Volume
- 5
- Category
- Article
- ISSN
- 1042-7163
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✦ Synopsis
3-Methy1-6,7-dihydrc~-SH-l,
2,4-th iadiazolo[4,5-a]
pyrimidine 4a reacted with isocyanates and isothiocyanates with elimination of acetonitrile and concomitant addition of two molecules of the heterocumubne togive the2,3-disubstituted-6,7-dihydro-SH-2ah4-thia-2, 3, 4a, ia-tetraazacyclopent[cd]indene-1 (2H),4(3H)-diones 8a-8e and the corresponding dithiones 9a-9h, respectively. 3-Methyl-5,lO-dihydrobenzo[e]-l,2,4-thiadiazolo[4,5-a] [ I ,3]diazepine 5a likewise reacted wilh isocyanates and isothiocyanates to give the 2,3-disubstituted-5,1 3,4a,3a,4-diol~es 10a-10f and the corresponding dithiones 1 la-llf. The base 4a reacted with phenyl isocyanate, methyl isothiocyanate, and phenyl isothiocyanate in toluene at room temperature to give the zwitterions 14a, 14b, and 14c, respectively, and the diazepine 5a reacted with phenyl isothiocyanate to give the zwitterion 17.
📜 SIMILAR VOLUMES
1,6ak 4 -Dithia-6-azapentalenes (7a)-( 7h), (12a), and (12b) have been synthesized by the reaction of 5-aryl-3-benzylidene-3H-1,2-dithioles with isonitriles in the presence of phosphoryl chloride and by the reaction of 3-benzyl-and 3-methyl-1k 4 , 2-dithiol-1-ylium salts with isonitriles. Possible m
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