Stereoselective synthesis of 3,4-disubstituted 1,2,5-thiadiazolidine 1,1-dioxides and their conversion to unsymmetrical vicinal diamines

Synlett

Volumn , Issue 6, 1998, Pages 623-624

  Pansare, Sunil V ^a   Rai, Anand N ^a   Kate, Sandesh N ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000562402     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1732     Document Type: Article

References (15)

1. a) Castro, J. L.; Matassa, V. G. J. Org. Chem. 1994, 59, 2289.
2. b) Sartor, D.; Saffrich, J.; Helmchen, G.; Richards, C. J.; Lambert, H. Tetrahedron Asymmetry 1991, 2, 639.
3. c) Ahn, K. H.; Yoo, D. J.; Kim. J. S. Tetrahedron Lett. 1992, 33, 6661.
4. a) McDermott, S. D.; Spillane, W. J. Org. Prep. Proc. Int. 1984, 16, 49 and references therein.
5. Baker, R. J.; Chiu, S. K.; Klein, C.; Timberlake, J. W.; Trefonas, L. M. J. Org. Chem. 1980, 45, 482.
6. a) Wright, J. B. J. Org. Chem. 1964, 29, 1905.
7. b) Vorreither, H. K.; Ziegler, E. Monatsh. Chem. 1965, 96, 216.
8. Pansare, S. V.; Malusare, M. G. Tetrahedron Lett. 1996, 37, 2859.
9. a) Nucleophilic additions to diarylidenesulfamides are known, see: Davis, F. A.; Giangiordano, M. A.; Starner, W. E. Tetrahedron Lett. 1986, 27, 3957.
10. b) Addition/elimination reactions of 3,4-dichloro 1,2,5-thiadiazole 1,1-dioxide with methanol and amines have been studied: Wen, R. Y.; Komin, A. P.; Street, R. W.; Carmack, M. J. Org. Chem. 1975, 40, 2743.
11. 3); MS (EI, 70 eV) m/z: 77 (40), 91 (4), 104 (100), 119 (98), 180 (5), 287 (M+1,1).
12. 2S: C, 62.47; H, 5.59; N, 9.71. Found: C, 62.29; H, 5.39; N, 9.61.
13. 3): 145.9 (ArC (ipso)), 141.5 (ArC, (ipso)), 128.1, 127.6, 127.2, 126.9, 126.2, 125.5 (ArC), 65.3 (CH), 58.1 (CNH), 26.3 (CH3); visible peaks for minor diastereomer: δ 64.5 (CH), 28.4 (CH3); MS (70cV, EI): m/z 77 (27), 91 (5), 104 (45), 120 (100), 227 (M+1, 1).
14. 6a (5% water/pyridine, reflux) which successfully cleaves substituted dibenzyl sulfamides is not applicable to 3, reasons for which are not obvious at present.
15. Pansare, S. V.; Malusare, M. G. Synlett 1997, 671.