A Stereoselective Route to trans-1-Arylthio-2-aminoindanes

Synlett

Volumn 1996, Issue 5, 1996, Pages 477-478

  Orlek, Barry S ^a  

^a GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0005752899     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5454     Document Type: Article

References (8)

1. B. S. Orlek, Tetrahedron Lett., 1986, 27, 1699.
2. T. L. Ho, Chem. Rev., 1975, 75, 1.
3. The preparation of N-2-arylthioethyl carboxamides from 2-alkyl oxazolines and aromatic thiols has been described: H. L. Wehrmeister, J. Org. Chem., 1963, 28, 2587.
4. 1H NMR. The chemical shift difference between the protons at C-3 in 4a-e falls in the range 0.65-0.9 ppm which is characteristic of trans 1,2-disubstituted indanes bearing an electron withdrawing substituent at the 1-position (see reference 1).
5. 2), 4.43 (1H, m, 2-H), 5.04 (1H, br s, 1-H), 5.48 (1H, d, J=6Hz, NH), 7.15-7.70 (8H, m, aromatic), 12.55 (1H, br s, NH). m.p. 154-156°C (ether-pentane).
6. 2), 4.42 (1H, m, 2-H), 4.53 (1H, br s, 1-H), 4.85 (1H, br s, NH), 7.18-7.50 (9H, m). m.p. 60.5-62°C (etherpentane).
7. 3) δ: 1.3 (3H, t, J=7Hz), 3.58 (2H, s), 4.22 (2H, q, J=7Hz), 6.51 (1H, s), 6.8 (1H, s), 7.0-7.3 (4H, m).
8. 1H NMR. In the absence of an acid catalyst no sign of 6 could be detected.