Synthesis of heterocycles by carbonylation of acetylenic compounds

Vizer, S. A.; Yerzhanov, K. B.; Quntar, Abed Al Aziz Al; Dembitsky, Valery M.

doi:10.1016/j.tet.2004.04.046

Cited by 77 publications

(21 citation statements)

References 119 publications

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“…The groups of Gabriele and Costa made impressive studies in this respect. With the catalysis of palladium, 2-prop-2-ynyloxyphenols underwent a tandem oxidative aminocarbonylation-cyclization to provide 2,3-dihydrobenzo [1,4]dioxine derivatives (Scheme 27). Reactions were carried out in the presence of catalytic amounts of PdI 2 in conjunction with an excess of KI in DMA under 20 atm of a 4:1 mixture of CO/air.…”

Section: Synthesis Of Five-membered Nitrogen-containing Heterocycles mentioning

confidence: 99%

“…Reactions were carried out in the presence of catalytic amounts of PdI 2 in conjunction with an excess of KI in DMA under 20 atm of a 4:1 mixture of CO/air. Under similar conditions, the reaction of 2-prop-2-ynyloxyanilines provides 3,4-dihydro-2H-benzo [1,4]oxazine as the product. For this reaction, the Z isomers were formed preferentially [88].…”

Section: Synthesis Of Five-membered Nitrogen-containing Heterocycles mentioning

confidence: 99%

“…Therefore, many efforts have been devoted to developing improved methods for synthesis of these compounds (for selected reviews on synthesis of heterocycles, see [1][2][3][4][5][6][7][8][9][10][11][12][13][14]). CO as the simplest C-1 unit has been widely used to construct carbonylated compounds (for selected examples, see [15][16][17][18][19][20][21][22][23][24][25][26]).…”

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Synthesis of Functionalized Heterocycles via Oxidative Carbonylation

Xing

2015

Topics in Heterocyclic Chemistry

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With the assistance of a proper oxidant, carbonylation of two nucleophiles can take place directly in carbonylation conditions, which is defined as oxidative carbonylation. This process starts with the reaction of nucleophiles with the metal catalyst in oxidation state (M (n + 2) ), followed by insertion of CO and subsequent reductive elimination, providing the carbonylated products and the metal catalyst in reduction state (M (n) ). The oxidant could reoxidize M (n) to M (n + 2) to promote the catalytic cycle. Oxidative carbonylation avoids the difficult oxidative addition of R-X to metal catalyst, so this kind of carbonylation could proceed in mild conditions. What's more is that oxidative carbonylation doesn't need prefunctionalization of substrates. So, it's no wonder that considerable attention has been drawn to construct important carbonylated compounds through oxidative carbonylation. Particularly, much progress in synthesis of carbonylated heterocycles via oxidative carbonylation has been achieved in the past decades. Here, we summarized the main achievements in this area from 1982 to the beginning of 2015.

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Section: Synthesis Of Five-membered Nitrogen-containing Heterocycles mentioning

confidence: 99%

Section: Synthesis Of Five-membered Nitrogen-containing Heterocycles mentioning

confidence: 99%

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confidence: 99%

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Synthesis of Functionalized Heterocycles via Oxidative Carbonylation

Xing

2015

Topics in Heterocyclic Chemistry

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“…As starting materials suitable to build the isoquinolinic skeleton, we envisioned the N-allylamides of the 2-iodobenzoic acids 3, easily available from the 2-iodobenzoyl chloride (1) In order to test the feasibility of the carbonylative cyclization of amides 3, we investigated the intramolecular reaction of N,N-diallylamide 3a in the presence of Et 3 N 4-[(Methoxycarbonyl)methyl]-3,4-dihydroisoquinolinones (2 equiv. ), MeOH (4 equiv.…”

Section: Resultsmentioning

confidence: 99%

“…[1] These reactions can take place with carbon monoxide incorporation into the cycle by a cyclocarbonylation process [2] or with a cyclization/carbonylation process with formation of rings having an exocylic carbonyl group. [3] In this field, despite not being as extensively studied as other Pd-catalyzed carbon-carbon bond-forming reactions, carbonylative cyclizations with vinyl or aryl halides bearing an ethylenic functionality were proven to be useful processes for the preparation of (hetero)aromatic carboxylic acid derivatives ( Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Palladium‐Catalyzed Cyclization/Carbonylation as a Direct Route to 4‐[(Methoxycarbonyl)methyl]‐3,4‐dihydroisoquinolinones

Ardizzoia¹,

Beccalli²,

Borsini³

et al. 2008

Eur J Org Chem

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An efficient synthetic protocol for the preparation of4‐[(methoxycarbonyl)methyl]‐3,4‐dihydroisoquinolin‐1‐onesfrom N‐allylamides of 2‐iodobenzoic acids has been performed under 100 atm of carbon monoxide. Pyridine ring formation occurs through an intramolecular Pd‐catalyzed carbon–carbon bond formation, followed by an alkoxycarbonylation process.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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Iron Acyl Complexes

Liebmann

Zastrow

Rück‐Braun

2014

Patai's Chemistry of Functional Groups

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This chapter covers a selection of acyl complexes and synthetic applications published within the past two decades. Iron acyl complexes are useful building blocks for organic synthesis. This survey covers recent synthetic applications of a selection of acyl complexes published within the last two decades. Herein, acyl complexes derived from carbonyl iron reagents are discussed, besides cyclopentadienyl dicarbonyl iron compounds, their phosphine‐substituted chiral‐at‐iron derivatives and diiron acyl complexes. This chapter has been organized according to the above classification with additional ligands and their reactivity, for example allyl, dienes.

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Synthesis of heterocycles by carbonylation of acetylenic compounds

Cited by 77 publications

References 119 publications

Synthesis of Functionalized Heterocycles via Oxidative Carbonylation

Synthesis of Functionalized Heterocycles via Oxidative Carbonylation

Palladium‐Catalyzed Cyclization/Carbonylation as a Direct Route to 4‐[(Methoxycarbonyl)methyl]‐3,4‐dihydroisoquinolinones

Iron Acyl Complexes

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