We have developed a copper-catalyzed synthesis of pyrrolo[2,1-]isoquinolines with terminal alkynes, aldehydes, and tetrahydroisoquinolines. A variety of pyrrolo[2,1-]isoquinolines have been prepared in 17-69% yield via a condensation/Mannich-type addition/oxidation/cyclization cascade sequence. Modifications through simple chemical transformations provided highly functionalized molecules containing a privileged framework.
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http://dx.doi.org/10.1021/acs.joc.2c01978 | DOI Listing |
Org Biomol Chem
June 2012
Division of Natural Products Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India.
One-pot synthesis of substituted pyrroles by a cascade reaction of azides with Morita-Baylis-Hillman acetates of acetylenic aldehydes is described and the reaction is efficiently mediated by triphenyl phosphine at room temperature. Sodium azide is successfully used to provide N-unsubstituted pyrroles, while alkyl azides afforded the corresponding N-alkylated pyrroles through a sequence of allylic substitution/azide reduction/cycloisomerization reactions. The obtained products have provided a new entry to indolizino indoles, pyrrolo isoquinolines and 8-oxo-5,6,7,8-tetrahydroindolizine.
View Article and Find Full Text PDFJ Am Chem Soc
June 2007
Department of Chemistry and Center for Chemical Methodology and Library Development (CMLD-BU), Boston University, Boston, Massachusetts 02215, USA.
J Pharmacol Exp Ther
December 1988
Department of Biological Research, McNeil Pharmaceutical, Spring House, Pennsylvania.
McN-5652 is one of a series of substituted pyrrolo-isoquinolines that, as a group, potently inhibit the uptake of one or more of the monoamines, norepinephrine, serotonin and dopamine. McN-5652 is characterized by exceptionally high potency as an inhibitor of the uptake of serotonin by rat brain synaptosomes in vitro (Ki approximately 0.6 nM) and ex vivo (ED50 approximately 2 mg/kg p.
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