Benzannulation via the reaction of ynamides and vinylketenes. Application to the synthesis of highly substituted indoles

TY Lam, YP Wang, RL Danheiser - The Journal of organic …, 2013 - ACS Publications
A two-stage “tandem strategy” for the synthesis of indoles with a high level of substitution on
the six-membered ring is described. Benzannulation based on the reaction of …

Synthesis of highly substituted quinolines via a tandem ynamide benzannulation/iodocyclization strategy

TP Willumstad, PD Boudreau… - The Journal of Organic …, 2015 - ACS Publications
A two-stage “tandem strategy” for the regiocontrolled synthesis of very highly substituted
quinolines is described. Benzannulation based on the reaction of cyclobutenones or diazo …

Synthesis of highly substituted indolines and indoles via intramolecular [4+ 2] cycloaddition of ynamides and conjugated enynes

JR Dunetz, RL Danheiser - Journal of the American Chemical …, 2005 - ACS Publications
Ynamides react with conjugated enynes in intramolecular [4+ 2] cycloadditions to afford
substituted indolines that undergo oxidation with o-chloranil to furnish the corresponding …

Benzannulation of aromatic heterocycles. A regiocontrolled method for construction of substituted benzo-and dibenzofurans and benzo-and dibenzothiophenes

LS Liebeskind, J Wang - The Journal of Organic Chemistry, 1993 - ACS Publications
4-Chloro-2, 3-disubstituted-2-cyclobutenones undergo palladium-catalyzed cross-coupling
with oxygen and sulfur heteroaryl tin reagents, and uponthermolysis at 100 C, good to high …

A [4+ 1] annulation approach to nitrogen heterocycles using 2, 3-bis (phenylsulfonyl)-1, 3-butadiene and primary amines

A Padwa, BH Norman - The Journal of Organic Chemistry, 1990 - ACS Publications
The reaction of amines with 2, 3-bis (phenylsulfonyl)-1, 3-butadiene affords pyrrolidines in
high yield. The formation of the nitrogen heterocycle involves initial conjugate addition and …

Synthesis of 1, 2-disubstituted indoles from α-aminonitriles and 2-halobenzyl halides

AK Bachon, T Opatz - The Journal of Organic Chemistry, 2016 - ACS Publications
The α-alkylation of deprotonated Strecker products derived from primary amines and
aromatic aldehydes with 2-halobenzyl halides furnishes intermediates that can be cyclized …

Annulation of aromatic imines via directed C− H bond activation

RK Thalji, KA Ahrendt, RG Bergman… - The Journal of Organic …, 2005 - ACS Publications
A directed C− H bond activation approach to the synthesis of indans, tetralins, dihydrofurans,
dihydroindoles, and other polycyclic aromatic compounds is presented. Cyclization of …

An annulation method for the synthesis of highly substituted polycyclic aromatic and heteroaromatic compounds

RL Danheiser, RG Brisbois, JJ Kowalczyk… - Journal of the …, 1990 - ACS Publications
A general strategy for thesynthesis of highly substituted polycyclic aromatic and
heteroaromatic compounds has been developed. The new aromatic annulation is …

Palladium-catalyzed annulation of haloanilines and halobenzamides using norbornadiene as an acetylene synthon: a route to functionalized indolines …

P Thansandote, DG Hulcoop, M Langer… - The Journal of Organic …, 2009 - ACS Publications
A general procedure for the palladium-catalyzed annulation of substituted haloanilines with
norbornadiene gives functionalized indolines in 51− 98% yield. These indolines can be …

Redox-neutral indole annulation cascades

MC Haibach, I Deb, CK De… - Journal of the American …, 2011 - ACS Publications
Aminobenzaldehydes react with indoles in an unprecedented cascade reaction. This acid-
catalyzed redox-neutral annulation proceeds via a condensation/1, 5-hydride shift/ring …