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Literature DB >> 29861552

A Photochemical Two-Step Formal [5+2] Cycloaddition: A Condensation/Ring-Expansion Approach to Substituted Azepanes.

Scott M Thullen^1,2, David M Rubush², Tomislav Rovis^1,2.

Abstract

Seven-membered nitrogen-containing heterocycles are considerably underrepresented in the literature compared to their five- and six-membered analogues. Herein, we report a relatively understudied photochemical rearrangement of N-vinylpyrrolidinones to azepin-4-ones in good yields. This transformation allows for the conversion of readily available pyrrolidinones and aldehydes to densely functionalized azepane derivatives in a facile two step procedure.

Entities: Chemical

Keywords: Photo-Fries rearrangement; [5+2] cycloaddition; azepane; heterocycles; photochemistry

Year: 2017 PMID： 29861552 PMCID： PMC5976449 DOI： 10.1055/s-0036-1589049

Source DB: PubMed Journal: Synlett ISSN： 0936-5214 Impact factor: 2.454

15 in total

1. Photochemical reactions as key steps in organic synthesis.

Authors: Norbert Hoffmann
Journal: Chem Rev Date: 2008-02-27 Impact factor: 60.622

2. Data-mining for sulfur and fluorine: an evaluation of pharmaceuticals to reveal opportunities for drug design and discovery.

Authors: Elizabeth A Ilardi; Edon Vitaku; Jon T Njardarson
Journal: J Med Chem Date: 2013-10-29 Impact factor: 7.446

3. Reaction control in synthetic organic photochemistry: switching between [5+2] and [2+2] modes of cycloaddition.

Authors: Claudio Roscini; Kara L Cubbage; Malcolm Berry; Andrew J Orr-Ewing; Kevin I Booker-Milburn
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

Review 4. Analysis of the structural diversity, substitution patterns, and frequency of nitrogen heterocycles among U.S. FDA approved pharmaceuticals.

Authors: Edon Vitaku; David T Smith; Jon T Njardarson
Journal: J Med Chem Date: 2014-10-07 Impact factor: 7.446

5. Catalytic enantioselective conjugate addition of dialkylzinc reagents to N-substituted-2,3-dehydro-4-piperidones.

Authors: Radovan Sebesta; Maria Gabriella Pizzuti; Arnold J Boersma; Adriaan J Minnaard; Ben L Feringa
Journal: Chem Commun (Camb) Date: 2005-02-02 Impact factor: 6.222

6. Formal intramolecular [5 + 2] photocycloaddition reactions of maleimides: a novel approach to the CDE ring skeleton of (-)-cephalotaxine.

Authors: K I Booker-Milburn; L F Dudin; C E Anson; S D Guile
Journal: Org Lett Date: 2001-09-20 Impact factor: 6.005

A Photochemical Two-Step Formal [5+2] Cycloaddition: A Condensation/Ring-Expansion Approach to Substituted Azepanes.

1. Photochemical reactions as key steps in organic synthesis.

2. Data-mining for sulfur and fluorine: an evaluation of pharmaceuticals to reveal opportunities for drug design and discovery.

3. Reaction control in synthetic organic photochemistry: switching between [5+2] and [2+2] modes of cycloaddition.

Review 4. Analysis of the structural diversity, substitution patterns, and frequency of nitrogen heterocycles among U.S. FDA approved pharmaceuticals.

5. Catalytic enantioselective conjugate addition of dialkylzinc reagents to N-substituted-2,3-dehydro-4-piperidones.

6. Formal intramolecular [5 + 2] photocycloaddition reactions of maleimides: a novel approach to the CDE ring skeleton of (-)-cephalotaxine.

7. Synthesis of amino acid derived enaminones via Wolff rearrangement using vinylogous amides as carbon nucleophiles.

Review 8. Structural relationships, distribution and biological activities of stemona alkaloids.

9. First higher-order photocycloaddition to a C=N bond: 1,3-diazepines from maleimides.

10. Synthesis of (±)-actinophyllic acid and analogs: applications of cascade reactions and diverted total synthesis.

1. Stereoselective Direct N-Trifluoropropenylation of Heterocycles with a Hypervalent Iodonium Reagent.

2. Modular Access to Azepines by Directed Carbonylative C-C Bond Activation of Aminocyclopropanes.