Ethoxycarbonylation of the 7-methylpyrrolotetrazolide ion revisited

Journal of Organic Chemistry

Volumn 61, Issue 16, 1996, Pages 5646-5647

  Moderhack, Dietrich ^a   Decker, Dirk ^a  

^a TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001255168     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960405v     Document Type: Article

References (15)

1. Dulcere, J.-P.; Tawil, M.; Santelli, M. J. Org. Chem. 1990, 55, 571.
2. (a) Moderhack, D.; Decker, D. 14th International Congress of Heterocyclic Chemistry, Antwerp, 1993; Abstracts of Papers, PO3-211, and references cited therein.
3. (b) Moderhack, D.; Decker, D. Heterocycles 1994, 37, 683.
4. Formed through lithiation of 3a or of (nondetectable) 1b.
5. Prepared from 1a in analogy to: Babichev, F. S.; Romanov, N. N. Ukr. Khim. Zh. 1973, 39, 49; Chem. Abstr. 1973, 78, 111229m. The 1H-isomeric structure of 3c is demonstrated by means of 3d, which has been made by an unambiguous route (cf. ref 2b).
6. Prepared from 1a in analogy to: Babichev, F. S.; Romanov, N. N. Ukr. Khim. Zh. 1973, 39, 49; Chem. Abstr. 1973, 78, 111229m. The 1H-isomeric structure of 3c is demonstrated by means of 3d, which has been made by an unambiguous route (cf. ref 2b).
7. Compare the influence exerted by an N(1)-attached carbamoyl group on the chemical shift of C(5) in 4,5-dihydro-1H-tetrazol-5-ones: Tsuge, O.; Urano, S.; Oe, K. J. Org. Chem. 1980, 45, 5130.
8. Cf. Abraham, R. J.; Lapper, R. D.; Smith, K. M.; Unsworth, J. F. J. Chem. Soc., Perkin Trans. 2 1974, 1004.
9. Cf. Begtrup, M.; Elguero, J.; Faure, R.; Camps, P.; Estopá, C.; Ilavský, D.; Fruchier, A.; Marzin, C.; de Mendoza, J. Magn. Reson. Chem. 1988, 26, 134.
10. Ege, G.; Heck, R.; Gilbert, K.; Irngartinger, H.; Huber-Patz, U.; Rodewald, H. J. Heterocycl. Chem. 1983, 20, 1629.
11. Moderhack, D.; Holtmann, B. Manuscript in preparation (compound made in analogy to the procedure outlined in ref 2b).
12. Alcalde, E.; Claramunt, R. M.; Elguero, J.; Saunderson Huber, C. P. J. Heterocycl. Chem. 1978, 15, 395.
13. For a synopsis of analytical instruments used, see: Moderhack, D. Liebigs Ann. 1996, 777.
14. Material described in ref 1 has mp 58-59 °C.
15. Peaks at m/e 168 and 143 (quoted in ref 1) were not observed.