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Structural assignment of regioisomeric 3-[2- or 5-anilino-2-(alkylamino)phenyl]propanoic acids, 2H-1,4-benzothiazin-3(4H)-ones and 2,3-dihydro-1,5-benzothiazepin-4(5H)-ones by 1D NOE and gHMBC NMR techniques

✍ Scribed by Alan R. Katritzky; Novruz G. Akhmedov; Mingyi Wang; Charles J. Rostek; Peter J. Steel

Publisher
John Wiley and Sons
Year
2004
Tongue
English
Weight
349 KB
Volume
42
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

The ^1^H and ^13^C NMR spectra of compounds 1–11 and 16–22 in CDCl~3~ and DMSO‐d~6~ solutions allowed structural assignment to regioisomers 1/5 and 2/6 and their regioselective cyclization products 16–18 utilizing one‐ and two‐dimensional NMR techniques (APT, DEPT, NOE difference, COSY, NOESY, HETCOR and gHMQC, gHMBC). Temperature‐dependent ^1^H NMR spectra of 8‐anilino‐5‐(4‐methyl‐2‐pentyl)‐2,3‐dihydro‐1,5‐benzothiazepin‐4(5__H__)‐one (18) indicated a free energy of activation (Δ__G__^‡^) of ca 17 kcal mol^−1^ for interconversion between rotamers. The ^1^H and ^13^C NMR spectra of 20 and 22 containing two chiral centers exhibit duplication of several signals, indicating the existence of two diastereomeric forms. The structure of 4 was unambiguously confirmed by x‐ray crystallography. Copyright © 2004 John Wiley & Sons, Ltd.

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