Perhydro-1,3-diazepine-2,4-diones by cyclization of 4-ureidobutyric acids with thionyl chloride: A reinvestigation

Journal of Heterocyclic Chemistry

Volumn 37, Issue 1, 2000, Pages 111-114

  Heckendorn, Roland ^a   Winkler, Tammo ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; BUTYRIC ACID DERIVATIVE; DIAZEPINE DERIVATIVE; PYRROLIDINE DERIVATIVE; THIOL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0034024156     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570370118     Document Type: Article

References (11)

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2. [b] A. Brandner, Synthesis 973 (1982);
3. [c] S. A. Avetisyan, S. L. Kocharov, L. V. Azaryan, A. A. Karapetyan, Yu. T. Struchov, Chem. Heterocyclic Compd. (Engl Transl.) 31, 28 (1995).
4. A. R. Katrizky and C. W. Rees, "Comprehensive Heterocyclic Chemistry", Ed. W. Lwowsky, Pergamon Press, Oxford, 1984 Vol. 7, pp 605-607.
5. J. Guillon, P. Sonnet, M. Boulouard, P. Dallemagne, H. Miel, M. Daoust, S. Rault, J. Heterocyclic Chem. 35, 535 (1998).
6. Examples from our laboratory are: [a] I. Sigg, G. Haas, T. Winkler, Helv. Chim. Acta 65, 275 (1982);
7. [b] G. Rihs, I. Sigg, G. Haas, T. Winkler, Helv. Chim. Acta 68, 1933 (1985);
8. [c] Y. P. Auberson, T. Winkler, Synthesis 470 (1994) (in this example, a six membered ring is preferred over a seven membered one).
9. 6 sulfoxide): 175.8, 141.8, 131.1, 128.8, 128.4, 48.4 (C-5), 39.1 (C-4), 37.6 ppm (C-3). W. Bencze, unpublished results.
10. SpecInfo Spectrum No. STCC-83275-657D, Chemical Concepts GmbH, Weinheim, Germany.
11. nd Ed., Ed. W. R. Croasmun and R.M. K. Carlson, VCH Publishers, New York 1994, p. 457 and references cited therein.