General and efficient organocatalytic synthesis of indoloquinolizidines, pyridoquinazolines and quinazolinones through a one-pot domino michael addition-cyclization-pictet-spengler or 1,2-amine addition reaction

Magnus Rueping; Chandra M.R. Volla; Michael Bolte; Gerhard Raabe

doi:10.1002/adsc.201100258

General and efficient organocatalytic synthesis of indoloquinolizidines, pyridoquinazolines and quinazolinones through a one-pot domino michael addition-cyclization-pictet-spengler or 1,2-amine addition reaction

Magnus Rueping^*, Chandra M.R. Volla, Michael Bolte, Gerhard Raabe

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

54 Scopus citations

Abstract

An asymmetric organocatalyzed reaction sequence involving a Michael addition of various 1,3-dicarbonyl compounds to α,β-unsaturated aldehydes with subsequent diastereoselective Pictet-Spengler cyclization has been developed. The substrate scope was found to be general and optically active indoloquinolizidines were isolated as single diastereomers in high yields with high to excellent enantioselectivites. In addition to tryptamine, the reaction has also been successfully applied to other nucleophiles including o-aminobenzylamine and anthranilamide giving rise to pyridoquinauolines and quinazolinones.

Original language	English (US)
Pages (from-to)	2853-2859
Number of pages	7
Journal	Advanced Synthesis and Catalysis
Volume	353
Issue number	14-15
DOIs	https://doi.org/10.1002/adsc.201100258
State	Published - Oct 2011
Externally published	Yes

Keywords

Brønsted acids
Lewis base catalyis
Mannich reaction
diarylprolinol ethers
multicomponent reaction

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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@article{c12911986ecd4501b8fceeb995f69ec0,

title = "General and efficient organocatalytic synthesis of indoloquinolizidines, pyridoquinazolines and quinazolinones through a one-pot domino michael addition-cyclization-pictet-spengler or 1,2-amine addition reaction",

abstract = "An asymmetric organocatalyzed reaction sequence involving a Michael addition of various 1,3-dicarbonyl compounds to α,β-unsaturated aldehydes with subsequent diastereoselective Pictet-Spengler cyclization has been developed. The substrate scope was found to be general and optically active indoloquinolizidines were isolated as single diastereomers in high yields with high to excellent enantioselectivites. In addition to tryptamine, the reaction has also been successfully applied to other nucleophiles including o-aminobenzylamine and anthranilamide giving rise to pyridoquinauolines and quinazolinones.",

keywords = "Br{\o}nsted acids, Lewis base catalyis, Mannich reaction, diarylprolinol ethers, multicomponent reaction",

author = "Magnus Rueping and Volla, {Chandra M.R.} and Michael Bolte and Gerhard Raabe",

year = "2011",

month = oct,

doi = "10.1002/adsc.201100258",

language = "English (US)",

volume = "353",

pages = "2853--2859",

journal = "Advanced Synthesis and Catalysis",

issn = "1615-4150",

publisher = "Wiley",

number = "14-15",

}

Rueping, M, Volla, CMR, Bolte, M & Raabe, G 2011, 'General and efficient organocatalytic synthesis of indoloquinolizidines, pyridoquinazolines and quinazolinones through a one-pot domino michael addition-cyclization-pictet-spengler or 1,2-amine addition reaction', Advanced Synthesis and Catalysis, vol. 353, no. 14-15, pp. 2853-2859. https://doi.org/10.1002/adsc.201100258

General and efficient organocatalytic synthesis of indoloquinolizidines, pyridoquinazolines and quinazolinones through a one-pot domino michael addition-cyclization-pictet-spengler or 1,2-amine addition reaction. / Rueping, Magnus; Volla, Chandra M.R.; Bolte, Michael et al.
In: Advanced Synthesis and Catalysis, Vol. 353, No. 14-15, 10.2011, p. 2853-2859.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - General and efficient organocatalytic synthesis of indoloquinolizidines, pyridoquinazolines and quinazolinones through a one-pot domino michael addition-cyclization-pictet-spengler or 1,2-amine addition reaction

AU - Rueping, Magnus

AU - Volla, Chandra M.R.

AU - Bolte, Michael

AU - Raabe, Gerhard

PY - 2011/10

Y1 - 2011/10

N2 - An asymmetric organocatalyzed reaction sequence involving a Michael addition of various 1,3-dicarbonyl compounds to α,β-unsaturated aldehydes with subsequent diastereoselective Pictet-Spengler cyclization has been developed. The substrate scope was found to be general and optically active indoloquinolizidines were isolated as single diastereomers in high yields with high to excellent enantioselectivites. In addition to tryptamine, the reaction has also been successfully applied to other nucleophiles including o-aminobenzylamine and anthranilamide giving rise to pyridoquinauolines and quinazolinones.

AB - An asymmetric organocatalyzed reaction sequence involving a Michael addition of various 1,3-dicarbonyl compounds to α,β-unsaturated aldehydes with subsequent diastereoselective Pictet-Spengler cyclization has been developed. The substrate scope was found to be general and optically active indoloquinolizidines were isolated as single diastereomers in high yields with high to excellent enantioselectivites. In addition to tryptamine, the reaction has also been successfully applied to other nucleophiles including o-aminobenzylamine and anthranilamide giving rise to pyridoquinauolines and quinazolinones.

KW - Brønsted acids

KW - Lewis base catalyis

KW - Mannich reaction

KW - diarylprolinol ethers

KW - multicomponent reaction

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DO - 10.1002/adsc.201100258

M3 - Article

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SN - 1615-4150

VL - 353

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JO - Advanced Synthesis and Catalysis

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ER -

General and efficient organocatalytic synthesis of indoloquinolizidines, pyridoquinazolines and quinazolinones through a one-pot domino michael addition-cyclization-pictet-spengler or 1,2-amine addition reaction

Abstract

Keywords

ASJC Scopus subject areas

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