In an article, author is Morak-Mlodawska, Beata, once mentioned the application of 147118-35-2, Name is (R)-Methyl 3-((tert-butyldimethylsilyl)oxy)-5-oxo-6-(triphenylphosphoranylidene)hexanoate, molecular formula is C31H39O4PSi, molecular weight is 534.7, MDL number is MFCD09753068, category is thiazines. Now introduce a scientific discovery about this category, Name: (R)-Methyl 3-((tert-butyldimethylsilyl)oxy)-5-oxo-6-(triphenylphosphoranylidene)hexanoate.
The double Smiles rearrangement in neutral conditions leading to one of 10-(nitropyridinyl)dipyridothiazine isomers
Phenothiazines are reported to exhibit very promising anticancer, antibacterial, antifungal, anti-inflammatory activities, reversal of multidrug resistance and many other actions. Synthesis of phenotiazines is mostly carried cyclization of o-aminodiphenyl sulfides proceeded through the Smiles rearrangement. The modifications of the phenothiazine structure via the substitution of the benzene ring with the pyridine ring gave various pyridobenzothiazines and dipyridothiazines. The reaction of 3-amino-3′-nitro-2,2′-dipyridinyl sulfide with 4-chloro-3-nitropyridine in sole DMF led to one of four possible isomeric nitropyridinyldipyridothiazines. Two-dimensional H-1 and C-13 NMR experiments (COSY, ROESY, HSQC and HMBC) were used to reveal the right product structure as 10-(3′-nitro-4′-pyridinyl) dipyrido[2,3-b; 2′,3′-e] [1,4]thiazine (10-(3′-nitro-4′-pyridinyl)-1,6-diazaphenothiazine). The final structure confirmation came from a single crystal X-ray analysis. This structure is the result of very rare reaction mechanism involving the double Smiles rearrangement of the S-N type. The tricyclic dipyridothiazine system is unexpectedly almost planar, with the butterfly angle of 176.39(4) between two pyridine rings and 174.17(6)degrees between the halves of the thiazine ring (the NCCS) planes. The pyridinyl substituent is rotated about N10-C11 bond and oriented almost perpendicularly to the tricyclic ring system with the dihedral angle between the two planar systems of 94.93(3)degrees. The nitropyridinyl substituent is located quasi-equatorially with the S center dot center dot center dot N10-C11 angle of 176.92(8)degrees. The nitro group is tilted from the pyridine ring by 128.44(8)degrees. (C) 2016 Elsevier B.V. All rights reserved.
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Reference:
Thiazine – an overview | ScienceDirect Topics,
,Thiazine | C4H5NS – PubChem