1100051-07-7Relevant articles and documents
Pd-Catalyzed One-Pot Stepwise Synthesis of Benzo[b][1,6]naphthyridines from 2-Chloroquinoline-3-carbonitriles Using Sulfur and Amines As Nucleophiles
Kumar, Ritush,Asthana, Mrityunjaya,Singh, Radhey M.
, p. 11531 - 11542 (2017)
A palladium-catalyzed one-pot stepwise coupling-annulation reaction of 2-chloroqunoline-3-carbonitriles enabled the direct synthesis of sulfur-substituted benzo[b][1,6]naphthyridines via multiple bond formation. The reaction provided an unusual mode for cyclization as sodium sulfide, a soft nucleophile, preferred to attack on the carbon of the nitrile group rather than on the C-C triple bond. The developed chemistry was extended with the secondary amines as nucleophiles to afford nitrogen-substituted benzo[b][1,6]naphythyridines while primary amines afforded hydroamination products. The hydromination products were transformed to benzo[b][1,6]naphthyridones via a base-mediated cyclization reaction. The developed protocol features inexpensive and easily synthesizable starting materials, easy operations, and a high efficiency and tolerance to a broad range of substrates.
Copper-free Sonogashira coupling of 2-chloroquinolines with phenyl acetylene and quick annulation to benzo[b][1,6]naphthyridine derivatives in aqueous ammonia
Chandra, Atish,Singh, Bhawana,Upadhyay, Shraddha,Singh, Radhey M.
experimental part, p. 11680 - 11685 (2009/04/11)
An efficient copper-free Sonogashira coupling of 2-chloroquinolines with phenyl acetylene to 2-ethynylquinolines is described. We further discussed the one pot facile annulation of 2-alkynylquinoline-3-carboxaldehydes to 3-phenylbenzo[b][1,6]naphthyridines in aqueous ammonia in excellent yield.
