So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Jiang, Bo; Fan, Wei; Sun, Mu-Yan; Ye, Qin; Wang, Shu-Liang; Tu, Shu-Jiang; Li, Guigen researched the compound: 1-Methyl-3-(thiophen-2-yl)-1H-pyrazol-5-amine( cas:118430-78-7 ).Electric Literature of C8H9N3S.They published the article 《Domino Reaction of Arylglyoxals with Pyrazol-5-amines: Selective Access to Pyrazolo-Fused 1,7-Naphthyridines, 1,3-Diazocanes, and Pyrroles》 about this compound( cas:118430-78-7 ) in Journal of Organic Chemistry. Keywords: domino heterocyclization arylglyoxal pyrazolamine pyrazolo naphthyridine diazocane pyrrole. We’ll tell you more about this compound (cas:118430-78-7).
New multicomponent domino reactions of arylglyoxals with pyrazol-5-amines have been established, providing selective access to unprecedented pyrazolo-fused 1,7-naphthyridines, 1,3-diazocanes, and pyrroles (up to 52 examples). The unreported dipyrazolo-fused 1,7-naphthyridines were regioselectively synthesized through a special double [3 + 2 + 1] heteroannulation accompanied by direct C-C formation between two electrophilic sites of arylglyoxals [e.g., PhCOCH(OH)2 + 1,3-dimethyl-5-pyrazolamine in presence of TsOH → I (70%)]. The unusual [3 + 3 + 1 + 1] cyclization resulted in 20 examples of novel dipyrazolo-fused 1,3-diazocanes [e.g., PhCOCH(OH)2 + 1-methyl-3-phenyl-5-pyrazolamine in presence of TsOH → II (71%)], whereas pyrrolo[2,3-c]pyrazoles were obtained in good yields by varying arylglyoxals and pyrazol-5-amines in the ratio 1:2 [e.g., PhCOCH(OH)2 + 1-phenyl-3-methyl-5-pyrazolamine in presence of TsOH → III (78%)]. Mechanisms of formation of these three new types of heterocycles are also proposed.
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Reference:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem