New Synthesis for norbornene from 4-amoniantipyrine

New Synthesis for norbornene from 4-amoniantipyrine

Silveira, Ingridhy Ostaciana Maia Freitas da; Winck, Cristiane Regina; Oliveira, Paola Dias de; Gomes, Roberto da Silva; Lima, Denis Pires de; Beatriz, Adilson

Abstract:

In 2006, Kas'yan et al. reported the synthesis of several bicycle [2.2.1] hept-5-ene-endo, endo-2, 3- dicarboxilic anhydride (endic anhydride) with cyclic non-aromatic amines. It is known that these compounds were used as components of repellent compositions and as agents endowed with sedative activity. One of the products formed was N-(1,5-dimethyl-3-oxo-2- phenyl-2,3-dihydro-1H-4 pyrazolyl) bicyclo [2.2.1] hept-5-ene-endo, endo-2,3-dicarboximide To prepare the compound 1 is required two steps: a) formation of a derivative norbornene acid and b) closure of imidic ring (Scheme 1) using several days with yields of 86% and 74%, respectively. In view of the synthetic and biological relevance, we proposed the synthesis of the compound (1) in 90 min. (Scheme 2), using three steps: a) synthesis of maleamic acid (4) derived from 4-aminoantypirine (3), b) synthesis of maleimide derived from compound (4) and c) 4+2 coupling reaction (Diels-Alder) using cyclopentadiene.

In 2006, Kas'yan et al. reported the synthesis of several bicycle [2.2.1] hept-5-ene-endo, endo-2, 3- dicarboxilic anhydride (endic anhydride) with cyclic non-aromatic amines. It is known that these compounds were used as components of repellent compositions and as agents endowed with sedative activity. One of the products formed was N-(1,5-dimethyl-3-oxo-2- phenyl-2,3-dihydro-1H-4 pyrazolyl) bicyclo [2.2.1] hept-5-ene-endo, endo-2,3-dicarboximide To prepare the compound 1 is required two steps: a) formation of a derivative norbornene acid and b) closure of imidic ring (Scheme 1) using several days with yields of 86% and 74%, respectively. In view of the synthetic and biological relevance, we proposed the synthesis of the compound (1) in 90 min. (Scheme 2), using three steps: a) synthesis of maleamic acid (4) derived from 4-aminoantypirine (3), b) synthesis of maleimide derived from compound (4) and c) 4+2 coupling reaction (Diels-Alder) using cyclopentadiene.

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DOI: 10.5151/chempro-15bmos-BMOS2013_20139217404

Referências bibliográficas

• [1] 1Kas’yan, L. I.; Pal’chikov, V. A.; Tarabara, I. N.; Krishchik, O. V.; Kas’yan, A. O.; Shishkina, S. V.; Shishkind. O. V. Russ. J. Org. Chem. 2006, 42,11, 1642.
• [2] 2US Patent 2824822, 1958; ref. Zh. Khim., 1960, 22, N92P.
• [3] 3Koch, H.; Kotlan, J.; Farkouh, E.; Lindner, M. Monatsh. Chem., 1971, 102, 609.

Como citar:

Silveira, Ingridhy Ostaciana Maia Freitas da; Winck, Cristiane Regina; Oliveira, Paola Dias de; Gomes, Roberto da Silva; Lima, Denis Pires de; Beatriz, Adilson; "New Synthesis for norbornene from 4-amoniantipyrine", p-17-17. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_20139217404