A straightforward synthesis of silylated and stannylated ynamines and ynehydrazines

Synthesis

Volumn , Issue 3, 1997, Pages 293-294

  Himbert, Gerhard ^a   Naßhan, Hans ^a   Gerulat, Oliver ^a  

^a Rheinland Pfälzische Technische Universität Kaiserslautern Landau   (Germany)

Author keywords

lithium amides; lithium trimehylhydrazide; N (1,2 dichlorovinyl) derivatives; N (silylethynyl , stannylethynyl)amines and trimethylhydrazines; trichloroethylene

Indexed keywords

ALKYNE DERIVATIVE; AMINE; HYDRAZINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0030920917     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1189     Document Type: Article

References (24)

1. Ficini, J.; Barbara, C. Bull. Soc. Chim. Fr. 1965, 2787.
2. Speciale, A. J.; Smith, L. R. J. Am. Chem. Soc. 1962, 84, 1868.
3. 5 synthesized the first (buta-1,3-diynyl)hydrazine derivatives. The main access to this class of compounds in these two papers represents the substitution of (alk-1-ynyl)halides by trimethylhydrazine or by the corresponding lithium salt.
4. de Croutte, H.; Janousek, Z.; Pongo, L.; Merényi, R.; Viehe, H. G. Bull. Soc. Chim. Fr. 1990, 127, 745.
5. Löffler, A.; Himbert, G. Synthesis 1994, 383.
6. Paley, M.S.; Frazier, D. O.; Abeledeyem, H.; McManus, S. P.; Zutaut, S. E. J. Am. Chem. Soc. 1992, 114, 3247.
7. Brandsma, L.; Mal'kina. A. G.; B. A. Trofimov, B. A. Synth. Commun. 1994, 24, 2721.
8. Viehe, H. G. In Chemistry of Acetylenes, Viehe, H. G., Ed.; Marcel Dekker: New York, 1969; p 861. Delavarenne, S.Y., Viehe, H. G. In Chemistry of Acetylenes, Viehe, H. G.; Ed.; Marcel Dekker: New York, 1969; p 651. Jäger, V. In Houben-Weyl, 4th ed., Vol. 5/2a; Müller, E., Ed.; Thieme: Stuttgart, 1977; p 33 ff. Collard-Motte, J.; Janousek, Z. Top. Curr. Chem. 1986, 130, 89. Himbert, G. In Houben-Weyl, 4th ed., Vol. E15; Kropf, H.; Schaumann, E., Eds.; Thieme: Stuttgart, 1993; p 3146.
9. Viehe, H. G. In Chemistry of Acetylenes, Viehe, H. G., Ed.; Marcel Dekker: New York, 1969; p 861. Delavarenne, S.Y., Viehe, H. G. In Chemistry of Acetylenes, Viehe, H. G.; Ed.; Marcel Dekker: New York, 1969; p 651. Jäger, V. In Houben-Weyl, 4th ed., Vol. 5/2a; Müller, E., Ed.; Thieme: Stuttgart, 1977; p 33 ff. Collard-Motte, J.; Janousek, Z. Top. Curr. Chem. 1986, 130, 89. Himbert, G. In Houben-Weyl, 4th ed., Vol. E15; Kropf, H.; Schaumann, E., Eds.; Thieme: Stuttgart, 1993; p 3146.
10. Viehe, H. G. In Chemistry of Acetylenes, Viehe, H. G., Ed.; Marcel Dekker: New York, 1969; p 861. Delavarenne, S.Y., Viehe, H. G. In Chemistry of Acetylenes, Viehe, H. G.; Ed.; Marcel Dekker: New York, 1969; p 651. Jäger, V. In Houben-Weyl, 4th ed., Vol. 5/2a; Müller, E., Ed.; Thieme: Stuttgart, 1977; p 33 ff. Collard-Motte, J.; Janousek, Z. Top. Curr. Chem. 1986, 130, 89. Himbert, G. In Houben-Weyl, 4th ed., Vol. E15; Kropf, H.; Schaumann, E., Eds.; Thieme: Stuttgart, 1993; p 3146.
11. Viehe, H. G. In Chemistry of Acetylenes, Viehe, H. G., Ed.; Marcel Dekker: New York, 1969; p 861. Delavarenne, S.Y., Viehe, H. G. In Chemistry of Acetylenes, Viehe, H. G.; Ed.; Marcel Dekker: New York, 1969; p 651. Jäger, V. In Houben-Weyl, 4th ed., Vol. 5/2a; Müller, E., Ed.; Thieme: Stuttgart, 1977; p 33 ff. Collard-Motte, J.; Janousek, Z. Top. Curr. Chem. 1986, 130, 89. Himbert, G. In Houben-Weyl, 4th ed., Vol. E15; Kropf, H.; Schaumann, E., Eds.; Thieme: Stuttgart, 1993; p 3146.
12. Viehe, H. G. In Chemistry of Acetylenes, Viehe, H. G., Ed.; Marcel Dekker: New York, 1969; p 861. Delavarenne, S.Y., Viehe, H. G. In Chemistry of Acetylenes, Viehe, H. G.; Ed.; Marcel Dekker: New York, 1969; p 651. Jäger, V. In Houben-Weyl, 4th ed., Vol. 5/2a; Müller, E., Ed.; Thieme: Stuttgart, 1977; p 33 ff. Collard-Motte, J.; Janousek, Z. Top. Curr. Chem. 1986, 130, 89. Himbert, G. In Houben-Weyl, 4th ed., Vol. E15; Kropf, H.; Schaumann, E., Eds.; Thieme: Stuttgart, 1993; p 3146.
13. Ott, E. Ber. Dtsch. Chem. Ges. 1942, 75, 1517. Riemschneider, R.; Brendel, K. Liebigs Ann. Chem. 1961, 640, 5. Pielichowski, J.; Popielarz, R. Synthesis 1984, 433.
14. Ott, E. Ber. Dtsch. Chem. Ges. 1942, 75, 1517. Riemschneider, R.; Brendel, K. Liebigs Ann. Chem. 1961, 640, 5. Pielichowski, J.; Popielarz, R. Synthesis 1984, 433.
15. Ott, E. Ber. Dtsch. Chem. Ges. 1942, 75, 1517. Riemschneider, R.; Brendel, K. Liebigs Ann. Chem. 1961, 640, 5. Pielichowski, J.; Popielarz, R. Synthesis 1984, 433.
16. Rademacher, P. In Houben-Weyl, 4th ed., Vol. E15; Kropf, H.; Schaumann, E., Eds.; Thieme: Stuttgart, 1993; p 598.
17. 8,1 3
18. Kantlehner, W. In Houben-Weyl, 4th ed., Vol. E15; Kropf, H.; Schaumann, E., Eds.; Thieme: Stuttgart, 1993; p 1942.
19. Delavarenne, S. Y.; Viehe, H. G. Chem. Ber. 1970, 103, 1209.
20. Ficini, J.; Duréault, A. C. R. Acad. Sci. 1971, Ser. C 273, 289.
21. Sato, Y.; Kobayashi, Y.; Sugiura, M.; Shirai, H. J. Org. Chem. 1978, 43, 199.
22. Himbert, G.; Feustel, M.; Jung, M. Liebigs Ann. Chem. 1981, 1907.
23. Feustel, M.; Himbert, G. Liebigs Ann. Chem. 1982, 196.
24. We did not succeed to obtain correct elemental analyses. But the structures of 5g and 5h are proved by spectral data and by chemical reactions. Gerulat. O.; Himbert, G.; Bergsträßer, U. Synlett 1995, 835.