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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.


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