Baylis-Hillman acetates in organic synthesis: convenient one-pot synthesis of α-carboline framework--a concise synthesis of neocryptolepine.
A convenient, facile, and one-pot methodology for the synthesis of α-carbolines from Baylis-Hillman (BH) acetates, involving three steps (reactions), (1) mono alkylation of 2-nitroarylacetonitriles with BH-acetates, (2) reduction of nitro group into amino group using Fe/AcOH and (3) formation of two (five and six membered) rings, is presented. This methodology is successfully applied to the synthesis of bioactive alkaloid neocryptolepine.
School of Chemistry, University of Hyderabad, Hyderabad, 500 046, India. dbsc@uohyd.ernet.in
Deevi
D
Basavaiah
Daggula
D
Mallikarjuna Reddy
D000085:Acetates / Q000138:chemical synthesis / Q000737:chemistry*; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000478:Alkylation; D029062:Apocynaceae / Q000737:chemistry; D002243:Carbolines / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry
D000085:Acetates; D000470:Alkaloids; D002243:Carbolines; D011804:Quinolines; C414982:neocryptolepine; C055571:alpha-carboline