The
cyclopenta[b]indole moiety represents a key
skeletal unit in several natural and synthetic compounds that exhibit
diverse biological properties. We described herein a two-step sequence
for synthesizing cyclopenta[b]indoles with great
structural diversity in overall yields up to 37%. The key step was
a palladium-catalyzed oxidative annulation of 3-alkylindoles (Fujiwara–Moritani
reaction). The obtained cyclopenta[b]indoles were
used as substrates in heterogeneous hydrogenation reactions to afford
new fused indolines in moderate yields. An acid-catalyzed intramolecular
cyclization of three such indolines gave tetracyclic lactams in 89,
90, and 61% yields.
Dedico esta dissertação aos meus pais, Sidnei Aparecido Agy e Aparecida Beatriz Capretz Agy. Muito obrigado pelo apoio e amor. AGRADECIMENTOS À minha família (Sidnei, Beatriz, Paula e Aline) pelo apoio e carinho. Ao professor Fernando Coelho, pela oportunidade de trabalhar em seu grupo de pesquisa, pela orientação e discussões construtivas, que contribuíram para o meu desenvolvimento pessoal e profissional. Obrigado por toda a sua ajuda, dedicação e paciência. Ao pós-doc e amigo, Manoel Trindade Rodrigues Jr. (Manolo), pela colaboração nos estudos com as tetraidroquinolinas, além das discussões e sugestões. Obrigado pela sua ajuda carinha! Aos amigos que fizeram ou fazem parte do
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