2009
DOI: 10.1016/j.tetlet.2008.10.086
|View full text |Cite
|
Sign up to set email alerts
|

Regioselective Diels–Alder cycloadditions and other reactions of 4,5-, 5,6-, and 6,7-indole arynes

Abstract: The regioselectivity of Diels-Alder cycloadditions of indole arynes (indolynes) at all three benzenoid positions was examined. Cycloadditions with the 4,5-and 5,6-indolynes, derived via metal-halogen exchange from the corresponding o-dibromo indoles, showed essentially no selectivity with 2-tbutylfuran. In contrast, the 6,7-indolyne displayed virtually complete preference for the more sterically congested cycloadduct. This same cycloadduct undergoes a facile acid-catalyzed rearrangement to afford the annulated… Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
1
1
1

Citation Types

1
11
0

Year Published

2009
2009
2021
2021

Publication Types

Select...
5
4

Relationship

1
8

Authors

Journals

citations
Cited by 47 publications
(12 citation statements)
references
References 28 publications
1
11
0
Order By: Relevance
“…The synthesis of two of the most potent members of a new class of tricyclic seven-membered lactam (SE-III-468 and SE-III-525) was carried out using the aryne cycloaddition strategies developed in the Buszek laboratories (Scheme 2) (59). In this manner, a collection of tertiary diene amides (prepared in four steps from Danheiser’s aldehyde) (10) was subjected to fluoride-induced decomposition of a tethered o-silyltriflate moiety to give the benzyne, which then underwent a facile intramolecular cycloaddition to afford directly the desired compounds.…”
Section: Methodsmentioning
confidence: 99%
See 1 more Smart Citation
“…The synthesis of two of the most potent members of a new class of tricyclic seven-membered lactam (SE-III-468 and SE-III-525) was carried out using the aryne cycloaddition strategies developed in the Buszek laboratories (Scheme 2) (59). In this manner, a collection of tertiary diene amides (prepared in four steps from Danheiser’s aldehyde) (10) was subjected to fluoride-induced decomposition of a tethered o-silyltriflate moiety to give the benzyne, which then underwent a facile intramolecular cycloaddition to afford directly the desired compounds.…”
Section: Methodsmentioning
confidence: 99%
“…Bound conformers of ligands interacting with the substrate binding sites of HMG-CoA reductase, including (A) the docked conformer of DL-II-D4, and (B) crystallographically resolved positions of mevastatin (lower left) and NADP + (upper right) as derived by superimposing relevant crystal structures 1HW8 (9) and 1DQ9 (10) onto our receptor model. All ligands are rendered as CPK-colored sticks.…”
Section: Figures and Tablesmentioning
confidence: 99%
“…In 2009, Buszek and co-workers developed a Fischer indole synthesis strategy to prepare Kobayashi precursors of 4,5-, 5,6-, and 6,7-indolynes . As shown in Scheme , hydrazine hydrochloride salt 12-53 could be prepared in 51% overall yield from 4-nitro-2-(trimethylsilyl)­phenol ( 12-52 ), which was then subjected to Fischer’s cyclization conditions with phenylacetaldehyde to afford indole products 12-54 and 12-55 in a 1:5 ratio.…”
Section: Hetaryne Chemistrymentioning
confidence: 99%
“…Valuable amidosubstituted aryne precursor 5 2o could be isolated in a modest 41% yield, which remains synthetically useful when compared to lengthy traditional methods for its preparation (typically 5À6 steps from commercially available o-halophenol). 14 The presence of electron-neutral or -donating alkyl or methoxy groups on the aromatic ring proved to be more challenging, owing to the formation of unidentified oxidative byproducts. Indeed, 3-methyl and 2-methyl aryltriflates 2h and 2p were obtained in 28 and 26% yield, respectively.…”
mentioning
confidence: 99%