Efficient one-pot synthesis of new 1-amino substituted pyrrolo[1,2-a]quinoline-4-carboxylate esters via copper-free Sonogashira coupling reactions

Ali Keivanloo; Shaghayegh Sadat Kazemi; Hossein Nasr-Isfahani; Abdolhamid Bamoniri

doi:10.1007/s11030-016-9694-7

Efficient one-pot synthesis of new 1-amino substituted pyrrolo[1,2-a]quinoline-4-carboxylate esters via copper-free Sonogashira coupling reactions

Mol Divers. 2017 Feb;21(1):29-36. doi: 10.1007/s11030-016-9694-7. Epub 2016 Sep 6.

Authors

Ali Keivanloo¹, Shaghayegh Sadat Kazemi², Hossein Nasr-Isfahani², Abdolhamid Bamoniri³

Affiliations

¹ School of Chemistry, Shahrood University of Technology, Shahrood, Iran. akeivanloo@yahoo.com.
² School of Chemistry, Shahrood University of Technology, Shahrood, Iran.
³ Chemistry Faculty, University of Kashan, Kashan, Iran.

PMID: 27599493
DOI: 10.1007/s11030-016-9694-7

Abstract

The reactions of several 2-chloroquinoline-3-carboxylate esters with propargyl alcohol and a secondary amine in the presence of palladium catalyst leads to the formation of new alkyl 1-amino substituted pyrrolo[1,2-a]quinoline-4-carboxylate derivatives. This one-pot process, carried out in the absence of any copper salt, provides an efficient method for the synthesis of functionalized pyrrolo[1,2-a]quinolines in good-to-high yields.

Keywords: Copper-free; Palladium catalyst; Propargyl alcohol; Pyrrolo[1,2-a]quinoline; Sonogashira coupling.

MeSH terms

Alkynes / chemistry
Carboxylic Acids / chemistry*
Catalysis
Chemistry Techniques, Synthetic
Esters
Quinolines / chemical synthesis*
Quinolines / chemistry*

Substances

Alkynes
Carboxylic Acids
Esters
Quinolines