Synthesis of 2-vinylic dihydroindoles and tetrahydroquinolines via Pd-catalyzed cross-coupling of o-alkenyl anilides with vinylic halides and triflates

Larock, Richard C.; Yang, Hoseok; Pace, Paola; Cacchi, Sandro; Fabrizi, Giancarlo

doi:10.1016/s0040-4039(98)00154-3

Cited by 30 publications

(7 citation statements)

References 5 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The palladium-catalyzed cross-coupling reaction between o -allylic or o -vinylic anilines 177 and vinylic halides or triflates 178 afforded tetrahydroquinolines or indolines 179 . It was found that the nature of the substituent on the nitrogen played a vital role in the reaction, with N -tosyl-substituted substrates generally giving higher yields.…”

Section: Synthesis Of 1234-tetrahydroquinolines Involving the Generat...mentioning

confidence: 99%

Advances in the Chemistry of Tetrahydroquinolines

2011

View full text Add to dashboard Cite

Involving the Generation of Two Bonds 5.1. Introduction 5.2. Formation of the NÀC 2 and C 3 ÀC 4 Bonds 5.2.1. DielsÀAlder Related Reactions 5.2.2. Tandem Michael AdditionÀCyclization Sequence 5.2.3. Miscellaneous Reactions 5.3. Formation of the NÀC 2 and C 4 ÀC 4a Bonds 5.3.1. Michael Addition Initiated Reactions 5.3.2. Miscellaneous Reactions 5.4. Formation of the NÀC 2 and C 2 ÀC 3 Bonds 5.5. Formation of the C 2 ÀC 3 and C 3 ÀC 4 Bonds 5.6. Formation of the C 2 ÀC 3 and C 4 ÀC 4a Bonds 5.7. Formation of the C 3 ÀC 4 and C 4 ÀC 4a Bonds 5.8. Formation of the C 8a ÀN and C 4 ÀC 4a Bonds 5.9. Formation of the NÀC 2 and C 8a ÀN Bonds 6. Synthesis of 1,2,3,4-Tetrahydroquinolines Involving the Generation of Three or More Bonds 6.1. Formation of the NÀC 2 , C 2 ÀC 3 , and C 4 ÀC 4a Bonds: The Povarov and Related Reactions

show abstract

Section: Synthesis Of 1234-tetrahydroquinolines Involving the Generat...mentioning

confidence: 99%

Advances in the Chemistry of Tetrahydroquinolines

2011

View full text Add to dashboard Cite

show abstract

“…A metal-free method involving the use of a new thiourea catalyst (106) has been reported for the preparation of 1,2-dihydroquinolines 107. The catalyst 106 activates organoboronic acids to facilitate the enantioselective Petasis transformation of quinolines to give substituted 1,2-dihydroquinolines 107 with a high degree of stereocontrol (Scheme 17.81) [205].…”

Section: Other Reactionsmentioning

confidence: 99%

Six‐Membered Heterocycles: Quinoline and Isoquinoline

Alajarı́n

Burgos

2011

Modern Heterocyclic Chemistry

View full text Add to dashboard Cite

“…Other methods utilize a nucleophilic aromatic cyclization reaction of an N -substituted aniline derivative containing a suitable π-acceptor, a 1,5-electrocyclization reaction, and a nucleophilic attack of styrene derivatives onto a transient nitrene species . Recently, Larock has reported that the palladium-catalyzed cross-coupling of o -vinylic and allylic anilides with vinylic halides and triflates produces dihydroindoles and tetrahydroquinolines . In all of these examples, the degree of substitution on the benzenoid portion of the molecule is set prior to the cyclization step.…”

Section: Introductionmentioning

confidence: 99%

A Cycloaddition Approach toward the Synthesis of Substituted Indolines and Tetrahydroquinolines

et al. 1999

View full text Add to dashboard Cite

The intramolecular Diels-Alder reaction of 2-substituted aminofurans (IMDAF) results in the formation of various indolines and tetrahydroquinolines. The isolation of these ring systems from the IMDAF reaction can be rationalized in terms of an initial [4 + 2]-cycloaddition that first produces an oxa-bridged cycloadduct, which was not detected since it readily underwent nitrogen-assisted ring opening. Proton exchange followed by an eventual dehydration provides the aromatic product. In certain cases, the intermediate cyclohexadienol can be isolated and independently converted to the final product in high yield. The starting 2-aminofurans were readily prepared from furanyl acyl azide by a Curtius rearrangement in the presence of an alcohol. Alkylation of the resulting N-alkyl carbamate with an alkenyl bromide allows for the synthesis of a wide variety of cycloaddition precursors. The scope of the IMDAF reaction was evaluated by using mono- and disubstituted alkenes, electron rich and electron deficient olefins, and acetylenic tethers. Cyclic 2-amidofurans were also synthesized using a related intramolecular Diels-Alder reaction of 2-amido-substituted oxazoles which contain a tethered alkyne. This transformation represents a new route to this rare heterocyclic ring system. The sequential cycloaddition method was used for a formal synthesis of the pyrrolophenanthridone alkaloid hippadine.

show abstract

Synthesis of 2-vinylic dihydroindoles and tetrahydroquinolines via Pd-catalyzed cross-coupling of o-alkenyl anilides with vinylic halides and triflates

Cited by 30 publications

References 5 publications

Advances in the Chemistry of Tetrahydroquinolines

Advances in the Chemistry of Tetrahydroquinolines

Six‐Membered Heterocycles: Quinoline and Isoquinoline

A Cycloaddition Approach toward the Synthesis of Substituted Indolines and Tetrahydroquinolines

Contact Info

Product

Resources

About