Directed ortho metalation - cross coupling links. Carbamoyl rendition of the baker-venkataraman rearrangement. Regiospecific route to substituted 4-hydroxycoumarins

Калинин, А. В.; Silva, Alcides J. M. da; Lopes, Claudio C.; Lopes, Rosângela S. C.; Snieckus, Victor

doi:10.1016/s0040-4039(98)00977-0

Cited by 62 publications

(29 citation statements)

References 22 publications

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“…The intramolecular ester condensation facilitates the acyl transfer and yields of C are generally good with conditions comparatively mild. This method was used for the preparation of chromones, 1,2 coumarines, 3,4 and benzindenopyrandiones. 5 The scope in the choice of residue R on the ester is broad and it can be aliphatic, olefinic, aromatic, or heteroaromatic, as investigated by Kraus et al 6 The construction of b-diketo side chains on an aromatic or quinoide nucleus is ideally suited for the synthesis of aromatic polyketide derived natural products and was used in the biomimetic-type synthesis of anthracylines 7 and angucyclines 8 (review 9 ).…”

Section: Introductionmentioning

confidence: 99%

First enantiospecific Baker–Venkataraman-rearrangements aiming at the total synthesis of chiral anthrapyran antibiotics

Krohn

Vidal

Vitz

et al. 2006

Tetrahedron: Asymmetry

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Section: Introductionmentioning

confidence: 99%

First enantiospecific Baker–Venkataraman-rearrangements aiming at the total synthesis of chiral anthrapyran antibiotics

Krohn

Vidal

Vitz

et al. 2006

Tetrahedron: Asymmetry

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“…Compound 2 was reacted with 4‐methyl‐2‐hydroxy‐acethophenone in pyridine solution at rt. The ester 12 was formed as an intermediate, and it was underwent Baker–Venkataraman [26] with KOH in one‐pot as an instance of domino reaction to obtain 1,3‐diketone compound 6 . Moreover, compound 6 was stirred in concentrated sulfuric acid at rt and gave the desired heterocyclic compound 7 .…”

Section: Resultsmentioning

confidence: 99%

An Entry into Obtaining Pyrazole‐, Chromone‐, or Oxadiazole‐Substituted 1H‐Pyrazoles via 2,3‐Furandiones

Çam

Bildirici

Mengeş

et al. 2013

Journal of Heterocyclic Chem

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“…Aside from the demonstrated DoMaAraAr cross-coupling connection above and the initial promise of acylative, 200 ! 201 (Scheme 49) [79] and carbonylative, 202 ! 203 !…”

Section: Interfacing Dom With Emerging Synthetic Methodsmentioning

confidence: 99%

The Directed ortho Metalation Reaction – A Point of Departure for New Synthetic Aromatic Chemistry

Hartung

Snieckus

2002

Modern Arene Chemistry

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159

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After a brief allusion to the current status of synthetic aromatic chemistry, a tour based on the Directed ortho Metalation (DoM) strategy is provided with selections from recent literature which highlight a) the use of DoM for the regiospecific preparation of polysubstituted aromatics and heteroaromatics; b) the valuable symbiosis of DoM with transition metal catalyzed AraAr cross-coupling protocols; c) the extension of DoM to the Directed remote Metalation (DreM) concept in biaryls, which provides methodologies for the construction of condensed aromatics (fluorenones, phenanthrols) and heterocyclics (thioxanthones, xanthones, acridones, dibenzphosphorinones, dibenzthiepinone dioxides, dibenzoxepinones, dibenzazepinones, dibenzphosphinones); and d) the evolving links of DoM to other modern methodologies with a note on the DoM-Grubbs ring-closing metathesis connection. The presentation is solely methodologically rather than total synthesis oriented; dependable directed metalation groups (DMGs ¼ CONR 2 , OCONR 2 , SONR 2 , NHBoc), new and renewed, are emphasized; p-excessive (furan, thiophene, indole) and p-deficient (pyridine) heterocycle HetDoM chemistry is delineated. While definitely not comprehensive, this account attempts to give a flavor of current anionic aromatic chemistry in synthesis. 10.1Scheme 1. Synthetic approaches to substituted aromatics. 10.2 The DoM Reaction as a Methodological Tool 331 Scheme 3. DoM chemistry generalizations. 10.2 The DoM Reaction as a Methodological Tool 333 Scheme 5. The N-cumyl sulfonamide DMG. Scheme 6. The N-cumyl carbamate DMG. 10.2 The DoM Reaction as a Methodological Tool 335 Scheme 9. The di-tert-butyl phosphine oxide DMG. 10.3 Heteroaromatic Directed ortho Metalation (HetDoM) in Methodological Practice 337

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Directed ortho metalation - cross coupling links. Carbamoyl rendition of the baker-venkataraman rearrangement. Regiospecific route to substituted 4-hydroxycoumarins

Cited by 62 publications

References 22 publications

First enantiospecific Baker–Venkataraman-rearrangements aiming at the total synthesis of chiral anthrapyran antibiotics

First enantiospecific Baker–Venkataraman-rearrangements aiming at the total synthesis of chiral anthrapyran antibiotics

An Entry into Obtaining Pyrazole‐, Chromone‐, or Oxadiazole‐Substituted 1H‐Pyrazoles via 2,3‐Furandiones

The Directed ortho Metalation Reaction – A Point of Departure for New Synthetic Aromatic Chemistry

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