Syntheses of chromones and quinolones via pd-catalyzed carbonylation of o-iodophenols and anilines in the presence of acetylenes

Torii, Sigeru; Okumoto, Hiroshi; Xu, Long; Sadakane, Masahiro; Shostakovsky, M. V.; Ponomaryov, A. B.; Калинин, В. Н.

doi:10.1016/s0040-4020(01)80421-x

Cited by 134 publications

(61 citation statements)

References 25 publications

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“…Although similar cyclizations were also known to give benzofuranones, 36 there was precedent suggesting that this undesired pathway might be avoided by first converting the ynone into a vinylogous amide. 37 Fortunately, we discovered that the vinylogous diethylamide derived from 98 did undergo acid-catalyzed cyclization to form the hydropyranone ring in 99 .…”

Section: Furans As Building Blocks For C-aryl Glycoside Synthesismentioning

confidence: 99%

Natural Products and Their Mimics as Targets of Opportunity for Discovery

Martin

2017

J. Org. Chem.

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Diverse structural types of natural products and their mimics have served as targets of opportunity in our laboratory to inspire the discovery and development of new methods and strategies to assemble polyfunctional and polycyclic molecular architectures. Furthermore, our efforts toward identifying novel compounds having useful biological properties led to the creation of new targets, many of which posed synthetic challenges that required the invention of new methodology. In this Perspective, selected examples of how we have exploited a diverse range of natural products and their mimics to create, explore, and solve a variety of problems in chemistry and biology will be discussed. The journey was not without its twists and turns, but the unexpected often led to new revelations and insights. Indeed, in our recent excursion into applications of synthetic organic chemistry to neuroscience, avoiding the more-traveled paths was richly rewarding.

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Section: Furans As Building Blocks For C-aryl Glycoside Synthesismentioning

confidence: 99%

Natural Products and Their Mimics as Targets of Opportunity for Discovery

Martin

2017

J. Org. Chem.

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“…4 Both stoichiometric strategies 5e8 and palladium catalyzed procedures have been reported for their synthesis. 9e14 Among these methods, the palladium catalyzed carbonylative coupling of 2-iodoanilines with arylacetylenes initially reported by Torii and co-workers 11,12 appears to be the most versatile as it gives generally good yields toward the expected compounds.…”

Section: Introductionmentioning

confidence: 99%

“…Therefore, under very similar conditions (2-iodoaniline, phenylacetylene, CO, palladium based catalyst) either six-membered-(4-quinolone, i.e., Torii 11,12 ) or five-membered ring compounds (indoxyl, i.e., Catellani 22 ) can be obtained as they are issued from the same non-cyclic intermediate (Scheme 1). However, these methods tend to give amide containing side-products or mixture of cyclized products along with the non-cyclic intermediate.…”

Section: Introductionmentioning

confidence: 99%

Heterogeneous metallo-organocatalysis for the selective one-pot synthesis of 2-benzylidene-indoxyl and 2-phenyl-4-quinolone

Genelot¹,

Dufaud²,

Djakovitch³

2011

Tetrahedron

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“…8 Since the initial discovery by Heck, 9 numerous variants of carbonylative cross-couplings have been disclosed. Competent coupling partners include aryl, alkenyl, alkynyl and alkyl organometallic reagents that may be derived from tin, 10 copper, 11 boron, 12 zinc, 13 aluminum, 14 magnesium 15 and silicon. 16 Recent developments in carbonylative cross-coupling technology have enabled use of alkyl halides in the reaction.…”

Section: Introductionmentioning

confidence: 99%

Facile access to sterically hindered aryl ketones via carbonylative cross-coupling: application to the total synthesis of luteolin

2011

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A general and mild protocol for achieving the carbonylative cross-coupling of sterically-hindered, ortho-disubstituted aryl ketones is reported. The commercially available PEPPSI-IPr catalyst is shown to efficiently promote the carbonylative cross-coupling of hindered ortho-disubstituted aryl iodides to give diaryl ketones; traditional phosphine catalysts are less effective. Carbonylative Suzuki-Miyaura cross-couplings provide a diverse array of biaryl ketones in good to excellent yields. The same catalyst is also shown to catalyze a carbonylative Negishi cross-coupling reaction, utilizing a variety of alkynyl zinc reagents to give the corresponding alkynyl aryl ketones. Application of this new methodology to the synthesis of the natural product luteolin is reported.

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Syntheses of chromones and quinolones via pd-catalyzed carbonylation of o-iodophenols and anilines in the presence of acetylenes

Cited by 134 publications

References 25 publications

Natural Products and Their Mimics as Targets of Opportunity for Discovery

Natural Products and Their Mimics as Targets of Opportunity for Discovery

Heterogeneous metallo-organocatalysis for the selective one-pot synthesis of 2-benzylidene-indoxyl and 2-phenyl-4-quinolone

Facile access to sterically hindered aryl ketones via carbonylative cross-coupling: application to the total synthesis of luteolin

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