Synthesis of Isoquinolines and Heterocycle-Fused Pyridines via Three-Component Cascade Reaction of Aryl Ketones, Hydroxylamine, and Alkynes.
Summary of "Synthesis of Isoquinolines and Heterocycle-Fused Pyridines via Three-Component Cascade Reaction of Aryl Ketones, Hydroxylamine, and Alkynes."
An efficient one-pot synthesis of isoquinolines and heterocycle-fused pyridines by three-component reaction of aryl ketones, hydroxylamine, and alkynes is developed. The reaction involves condensation of aryl ketones and hydroxylamine, rhodium(III)-catalyzed C-H bond activation of the in situ generated aryl ketone oximes, and cyclization with internal alkynes. This protocol enables rapid assembly of multisubstituted isoquinolines as well as γ-carbolines, furo[2,3-c]pyridines, thieno[2,3-c]pyridines, and benzofuro[2,3-c]pyridines from readily available substrates.
Affiliation
Department of Chemistry, Tsinghua University , Key Laboratory of Organic Optoelectronics & Molecular Engineering of Ministry of Education, Beijing 100084, China.
Journal Details
This article was published in the following journal.
Name: The Journal of organic chemistry
ISSN: 1520-6904
Pages: 5794-800
Links
- PubMed Source: http://www.ncbi.nlm.nih.gov/pubmed/22702218
- DOI: http://dx.doi.org/10.1021/jo3010414
Medical and Biotech [MESH] Definitions
Pyrroloiminoquinones
Derivatives of QUINOLINES with fused PYRROLES and a keto group or INDOLEQUINONES with fused PIPERIDINES.
Azulenes
Compounds based on a seven-membered ring fused to a five-membered ring. Heat can rearrange them to NAPHTHALENES which have two fused six-membered rings. They are similar to guaiazulenes which are SESQUITERPENES with a six-membered ring fused to a five-membered ring.
Benzylisoquinolines
ISOQUINOLINES with a benzyl substituent.
Naphthalimides
Compounds with three fused rings that appear like a naphthalene fused to piperidone or like a benz(de)isoquinoline-1,3-dione (not to be confused with BENZYLISOQUINOLINES which have a methyl separating the naphthyl from the benzyl rings). Members are CYTOTOXINS.
Picolines
A group of compounds that are monomethyl derivatives of pyridines. (From Dorland, 28th ed)
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