title: Synthesis of indolylquinolines, indolylacridines, and indolylcyclopenta[b]quinolines from the Baylis-Hillman adducts: an in situ [1,3]-sigmatropic rearrangement of an indole nucleus to access indolylacridines and indolylcyclopenta[b]quinolines.
abstract: A simple and easy route to the synthesis of a variety of structurally diverse indolylquinolines, indolylacridines, and indolylcyclopenta[b]quinoline derivatives via the reductive cyclization of C-alkylated indole derivatives, derived from acyclic as well as cyclic Baylis-Hillman adducts with indoles, is described. An unusual in situ [1,3]-sigmatropic rearrangement of the indole nucleus was observed during the reductive cyclicization of α-regioselective B-H adducts containing indoles to produce indolylacridines and indolylcyclopenta[b]quinoline derivatives.
authors.affiliation: Department of Chemistry, National Taiwan Normal University, 88, Section 4, Tingchow Road, Taipei, Taiwan 116, Republic of China.
authors.forename: Chintakunta
authors.initials: C
authors.lastname: Ramesh
authors.forename: Po-Min
authors.initials: PM
authors.lastname: Lei
authors.forename: Donala
authors.initials: D
authors.lastname: Janreddy
authors.forename: Veerababurao
authors.initials: V
authors.lastname: Kavala
authors.forename: Chun-Wei
authors.initials: CW
authors.lastname: Kuo
authors.forename: Ching-Fa
authors.initials: CF
authors.lastname: Yao
mesh_terms: D000166:Acridines / Q000138:chemical synthesis* / Q000737:chemistry; D000478:Alkylation; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000166:Acridines; D007211:Indoles; D011804:Quinolines