Substituted tetralins IV: Synthesis and stereochemistry of 4,4-disubstituted 1,2,3,4-tetrahydro-2-naphthoic acids
β Scribed by Ezzat M. Kandeel; Leray J. Anderson; John H. Block; Allen I. White; Arnold R. Martin
- Publisher
- John Wiley and Sons
- Year
- 1972
- Tongue
- English
- Weight
- 462 KB
- Volume
- 61
- Category
- Article
- ISSN
- 0022-3549
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β¦ Synopsis
The syntheses of four 4-methyl-4-phenyl-l,2,3,4-tetrahydro-Znaphthoic acids are described. The stereospecific cyclization of the cis-isomers and proton NMR studies establishing cistrans product ratios are also reported.
Keyphrases 0 Tetralins, substituted-synthesis, stereochemistry of 4,4-disubstituted 1,2,3,4-tetrahydro-Z-naphthoic acids 0 1,2,3,4-Tetrahydro-2-naphthoic acids, 4,4-disubstituted-synthesis, stereochemistry NMR spectroscopy-determination, stereochemistry of 4.4-disubstituted 1,2,3,4-tetrahydro-Z-naphthoic acids I J Stereochemistry of 4,4-disubstituted 1,2,3,4-tetrahydro-Z-naphthoic acids-determination, NMR spectroscopy
Because of continuing interest in the analgesic (1, 2) and cardiac antiarrhythmic (3, 4) properties of various substituted 2-aminotetralin derivatives, the synthesis and pharmacological evaluation of the isomers of N,N-* Melting points were determined on a calibrated Fisher-Johns melting-point block. Microanalyses were performed by the Galbraith Laboratories, Knoxville, Tenn. IR spectra were obtained with Beckman IR-5 and IR-8 spectrophotometers. NMR spectra were obtained with a Varian A-60 spectrometer, using approximately 15 % concentrations of compound in carbon tetrachloride or deuterochloroform, with tetramethylsilane as an internal standard.
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Two new and efficient synthetic routes towards substituted 4H-1,4-benzoxazine derivatives were reported. The first one involves the synthesis in four steps of the 4-Boc-4H-1,4-benzoxazine and its regioselective substitution on C-3 following a lithiation-electrophilic substitution sequence. The secon
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