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7 article(s) from Krasavin, Mikhail

A novel spirocyclic scaffold accessed via tandem Claisen rearrangement/intramolecular oxa-Michael addition

Anastasia Vepreva,
Alexander Yanovich,
Dmitry Dar’in,
Grigory Kantin,
Alexander Bunev and
Mikhail Krasavin

Full Research Paper
Published 06 Dec 2022

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1. Graphical Abstract
2. Figure 1: Examples of approved spirocyclic drugs.
  
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3. Scheme 1: (a) Earlier reported Rh(II)-catalyzed spirocyclization of DAS with the formation of minor enol ethe...
  
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4. Scheme 2: Initial attempt at Rh(II)-catalyzed O–H insertion/Claisen rearrangement.
  
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5. Scheme 3: Rh₂(esp)₂-catalyzed O–H insertion reactions between various DAS 1 and phenols.
  
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6. Scheme 4: Two-step, one-pot sequence of the Claisen rearrangement/intramolecular Michael-type spirocyclizatio...
  
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7. Scheme 5: Tentative rationalization of the diastereoselectivity observed in all 5→7 transformations (shown fo...
  
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Graphical Abstract

Beilstein J. Org. Chem. 2022, 18, 1649–1655, doi:10.3762/bjoc.18.177

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A novel bis-triazole scaffold accessed via two tandem [3 + 2] cycloaddition events including an uncatalyzed, room temperature azide–alkyne click reaction

Ksenia Malkova,
Andrey Bubyrev,
Vasilisa Krivovicheva,
Dmitry Dar’in,
Alexander Bunev and
Mikhail Krasavin

Letter
Published 02 Dec 2022

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1. Graphical Abstract
2. Figure 1: (a) Previously developed three-component approach to 1,5-disubstituted 1,2,3-triazoles; (b) double ...
  
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3. Scheme 1: Results of a trial reaction between 1, o-azidobenzaldehyde (3a) and propargylamine.
  
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4. Figure 2: Diversely bioactive compounds based on scaffolds A and B.
  
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5. Scheme 2: Three-component reaction of 1, propargylamine and various o-azidobenzaldehydes.
  
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6. Figure 3: Aromatic azido aldehydes 3j–l that failed to react with 1 and propargylamine.
  
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7. Scheme 3: Variations of the amine component in the reactions with 1 and 3a.
  
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Graphical Abstract

Beilstein J. Org. Chem. 2022, 18, 1636–1641, doi:10.3762/bjoc.18.175

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Facile and diastereoselective arylation of the privileged 1,4-dihydroisoquinolin-3(2H)-one scaffold

Dmitry Dar’in,
Grigory Kantin,
Alexander Bunev and
Mikhail Krasavin

Letter
Published 22 Aug 2022

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1. Graphical Abstract
2. Figure 1: Diverse bioactive compounds based on the privileged 1,4-DHIQ scaffold.
  
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3. Figure 2: Strategy investigated in this work.
  
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4. Scheme 1: Preparation of 3(2H)-isoquinolones 11. ^aObtained as a 10:1 mixture of regioisomers; purified by cry...
  
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5. Scheme 2: Preparation of 4-diazo-3(2H)-isoquinolones 10. ^aConfirmed by single-crystal X-ray crystallography (...
  
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6. Scheme 3: TfOH-promoted arylation of diazo substrates 10. ^aStructure confirmed by single-crystal X-ray analys...
  
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7. Scheme 4: Unexpected outcome of the TfOH-promoted arylation of 10a with N-formyl-N-methylaniline giving rise ...
  
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8. Scheme 5: Plausible mechanism for the conversion of diazo substrates 10 to 4-aryl products 9 (shown for ArH =...
  
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Graphical Abstract

Beilstein J. Org. Chem. 2022, 18, 1070–1078, doi:10.3762/bjoc.18.109

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Unusual highly diastereoselective Rh(II)-catalyzed dimerization of 3-diazo-2-arylidenesuccinimides provides access to a new dibenzazulene scaffold

Anastasia Vepreva,
Alexander S. Bunev,
Andrey Yu. Kudinov,
Grigory Kantin,
Mikhail Krasavin and
Dmitry Dar’in

Letter
Published 11 May 2022

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1. Graphical Abstract
2. Figure 1: Previously reported transformations of DAS (1) and their unusual dimerization investigated in this ...
  
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3. Scheme 1: The result of Rh(II)-catalyzed decomposition of DAS 1r.
  
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4. Scheme 2: Plausible mechanism for the formation of dimer 2a and indene 3a through the Rh(II)-catalyzed decomp...
  
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5. Figure 2: Cytotoxicity of N-alkyl-substituted dibenzoazulenodipyrroles 2 against the A549 human lung adenocar...
  
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Graphical Abstract

Beilstein J. Org. Chem. 2022, 18, 533–538, doi:10.3762/bjoc.18.55

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Preparation and in situ use of unstable N-alkyl α-diazo-γ-butyrolactams in Rh^II-catalyzed X–H insertion reactions

Maria Eremeyeva,
Daniil Zhukovsky,
Dmitry Dar’in and
Mikhail Krasavin

Letter
Published 02 Apr 2020

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1. Graphical Abstract
2. Figure 1: Previously reported uses of α-diazo-γ-butyrolactams 1 and 4.
  
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3. Scheme 1: Generation and in situ Rh^II-catalyzed X–H insertion reactions of the diazo compounds 4a–c. Conditio...
  
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4. Scheme 2: Formation of the enamine coupling products 8a and b.
  
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Graphical Abstract

Beilstein J. Org. Chem. 2020, 16, 607–610, doi:10.3762/bjoc.16.55

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A three-component, Zn(OTf)₂-mediated entry into trisubstituted 2-aminoimidazoles

Alexei Lukin,
Anna Bakholdina,
Anna Kryukova,
Alexander Sapegin and
Mikhail Krasavin

Letter
Published 07 May 2019

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1. Graphical Abstract
2. Figure 1: Examples of imidazole (1 and 2) and oxazole (3) syntheses from propargylamides previously reported ...
  
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3. Figure 2: Substrate scope for the three-component synthesis of 5.
  
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4. Figure 3: Plausible mechanism for the formation of 5.
  
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Graphical Abstract

Beilstein J. Org. Chem. 2019, 15, 1061–1064, doi:10.3762/bjoc.15.103

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A speedy route to sterically encumbered, benzene-fused derivatives of privileged, naturally occurring hexahydropyrrolo[1,2-b]isoquinoline

Olga Bakulina,
Alexander Ivanov,
Vitalii Suslonov,
Dmitry Dar’in and
Mikhail Krasavin

Full Research Paper
Published 18 Jul 2017

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1. Graphical Abstract
2. Figure 1: The Castagnoli–Cushman reaction (CCR).
  
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3. Figure 2: Assembly of hexahydropyrrolo[1,2-b]isoquinoline core via the CCR and its occurrence in natural and ...
  
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4. Figure 3: Indolenine substrates 9a–t investigated in this work. ^aPrepared for the first time (the rest are kn...
  
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5. Figure 4: Anti- and syn-diastereomers of 10 and 10'.
  
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6. Figure 5: Single-crystal X-ray structure of compound 10l.
  
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7. Scheme 1: Formation of unwanted products 11 and 12 in lieu of the CCR with 9p–t.
  
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8. Figure 6: Typical J(H¹¹-H^11a)-values and corresponding dihedral angles for syn- and anti-diastereomers of com...
  
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9. Figure 7: The difference in the ¹³C NMR chemical shifts of the angular methyl group between syn- and anti-dia...
  
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10. Figure 8: Criteria for stereochemistry assignment of anti-10o.
  
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11. Scheme 2: Syn/anti isomerization of compound 10e.
  
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12. Scheme 3: Alternative mechanistic pathways for the CCR.
  
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13. Scheme 4: Formation and fate of Mannich adduct 13e.
  
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14. Scheme 5: Mechanistic rationale for the 13e→ syn/anti-10e conversion.
  
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15. Scheme 6: Decarboxylation of anti/syn-10h.
  
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Graphical Abstract

Beilstein J. Org. Chem. 2017, 13, 1413–1424, doi:10.3762/bjoc.13.138

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