The Aza‐Prins Reaction in the Synthesis of Natural Products and Analogues
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DOI: 10.1002/ejoc.201601411
Abstract: The classical Prins cyclization reaction has been one of the most studied reactions during the last two decades and it has found many applications in key steps of natural product syntheses, especially for products containing… read more here.
Keywords: natural products; prins reaction; reaction; prins cyclization ... See more keywords
Synthesis of Spirocyclic Isoindolones Using an Alkynyl aza-Prins/Oxidative halo-Nazarov Cyclization Sequence.
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DOI: 10.1021/acs.orglett.1c00191
Abstract: In this report, we describe an alkynyl halo-aza-Prins cyclization of 3-hydroxyisoindolones to prepare aza-Prins products. These Prins adducts undergo oxidation at the 3-isoindolone position after activation of the amide by triflic anhydride and 2-chloropyridine to… read more here.
Keywords: nazarov cyclization; aza prins; halo nazarov; halo ... See more keywords
Synthesis of Six-Membered Spiro Azacyclic Oxindole Derivatives via a One-Pot Process of Umpolung Allylation/Aza-Prins Cyclization.
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DOI: 10.1021/acs.orglett.1c00292
Abstract: An unprecedented synthetic approach involving umpolung allylation/aza-Prins cyclization of N-2,2,2-trifluoroethylisatin ketimines is described. The reactions proceed smoothly with allyl bromide in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene, H2O, and trimethylsilyl bromide; this one-pot protocol allows access to… read more here.
Keywords: umpolung allylation; one pot; prins cyclization; aza prins ... See more keywords
Total Synthesis of the Caged Indole Alkaloid Arboridinine Enabled by aza-Prins and Metal-Mediated Cyclizations.
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DOI: 10.1021/jacs.7b07724
Abstract: Although alkaloid natural products possess incredible diversity when considered broadly, certain domains are sometimes shared by several members, even from different sub-collections. Such homology can point to potential synthetic strategies. Herein, we highlight how such… read more here.
Keywords: metal mediated; arboridinine; aza prins; total synthesis ... See more keywords
Synthesis of pyrimido[2,1-a]isoindolone and isoindolo[2,1-a]quinazolinone via intramolecular aza-Prins type reaction.
Sign Up to like & getrecommendations! Published in 2021 at "Chemical communications"
DOI: 10.1039/d1cc04554g
Abstract: A novel aza-Prins type cyclization reaction involving N-acyliminium ions and amides is reported for the synthesis of tetrahydropyrimido[2,1-a]isoindole-2,6-dione and 6,6a-dihydroisoindolo[2,1-a]quinazoline-5,11-dione derivatives in excellent yields. The strategy features inexpensive reagents, mild reaction conditions, and metal-free synthesis… read more here.
Keywords: prins type; reaction; synthesis pyrimido; aza prins ... See more keywords