The double Smiles rearrangement in neutral conditions leading to one of 10-(nitropyridinyl)dipyridothiazine isomers

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• 作者：Beata Morak-Młodawska^a ; Krystian Pluta^a ; ^{pluta@sum.edu.pl} ; Kinga Suwińska^b ; ^c ; Małgorzata Jeleń^a
• 关键词：Phenothiazines ; Dipyrido-1 ; 4-thiazines ; Double Smiles rearrangement ; Thiazine ring formation ; 2D NMR spectra ; X-ray analysis
• 刊名：Journal of Molecular Structure
• 出版年：2017
• 出版时间：5 April 2017
• 年：2017
• 卷：1133
• 期：Complete
• 页码：398-404
• 全文大小：1033 K
• 卷排序：1133

文摘

The phenothiazine system was modified with the pyridine moiety. The very rare double Smiles rearrangement of the SN type was observed. The reaction could lead to four isomeric nitropyridinyl dipyridothiazines. The rearrangement pathway was concluded from NOESY, COSY, HSQC and HMBC spectra. X-ray analysis showed unexpectedly planar dipyridothiazine ring system.