Cerium(III)-Catalyzed Facile Synthesis of Dihydrobenzofuran-Tethered Pyridines and Dihydroquinolin-5(6H)-ones from beta-Enaminones

A series of novel dihydrobenzofuran-tethered pyridines, dihydroquinolin-5(6H)-ones, and indeno[1,2-b]pyridin-5-ones were synthesized in very good yields by CeCl3 center dot 7H(2)O-NaI catalyzed one-pot condensation of variants of the Bohlmann-Rahtz reaction, viz. beta-enaminones derived from 7-acety...

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 21; pp. 3745 - 3754
Main Authors Kantevari, Srinivas, Addla, Dinesh, Sridhar, Balasubramanian
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.11.2010
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Bohlmann-Rahtz reaction
LEWIS-ACID PROMOTER
DIMETHYL SULFOMYCINAMATE
CeCl3 center dot 7HO-NaI
DICARBONYL COMPOUNDS
one-pot condensation
beta-enaminone
quinolinones
MULTICOMPONENT REACTIONS
pyridines
DIVERSITY-ORIENTED SYNTHESIS
2,3,6-TRISUBSTITUTED PYRIDINES
dihydrobenzofuran
heterocycles
BENZOFURANS
THIOPEPTIDE ANTIBIOTICS
EFFICIENT
DERIVATIVES
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Summary:A series of novel dihydrobenzofuran-tethered pyridines, dihydroquinolin-5(6H)-ones, and indeno[1,2-b]pyridin-5-ones were synthesized in very good yields by CeCl3 center dot 7H(2)O-NaI catalyzed one-pot condensation of variants of the Bohlmann-Rahtz reaction, viz. beta-enaminones derived from 7-acetyldihydrobenzofurans, acyclic and cyclic 1,3-dicarbonyls, and ammonium acetate. The protocol offers the advantages of easily accessible substrates, shorter reaction times, and easy work-up with a readily available catalyst. Further more, dihydrobenzofuran-substituted 2-(chloromethyl)pyridine was derivatized to its synthetic hybrid by reacting with piperazine.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0030-1258236