Literature DB >> 24052668

Facile Access to Ring-Fused Aminals via Direct α-Amination of Secondary Amines with ortho-Aminobenzaldehydes. Synthesis of Vasicine, Deoxyvasicine, Deoxyvasicinone, Mackinazolinone and Ruteacarpine.

Matthew T Richers1, Indubhusan Deb, Alena Yu Platonova, Chen Zhang, Daniel Seidel.   

Abstract

Secondary amines undergo redox-neutral reactions with aminobenzaldehydes under conventional and microwave heating to furnish polycyclic aminals via amine α-amination/N-alkylation. This unique α-functionalization reaction proceeds without the involvement of transition metals or other additives. The resulting aminal products are precursors for various quinazolinone alkaloids and their analogues.

Entities:  

Keywords:  Aminals; C–H bond functionalization; Friedländer condensation; Quinazolinone alkaloids; Redox Isomerization

Year:  2013        PMID： 24052668      PMCID： PMC3774014     

Source DB:  PubMed          Journal:  Synthesis (Stuttg)        ISSN： 0039-7881            Impact factor:   3.157


  94 in total

1.  A novel one-pot synthesis of some new interesting pyrrole derivatives.

Authors:  Javad Azizian; Ali Reza Karimi; Zahra Kazemizadeh; Ali A Mohammadi; Mohammad R Mohammadizadeh
Journal:  J Org Chem       Date:  2005-02-18       Impact factor: 4.354

2.  Aplaminal: a novel cytotoxic aminal isolated from the sea hare Aplysia kurodai.

Authors:  Takeshi Kuroda; Hideo Kigoshi
Journal:  Org Lett       Date:  2008-01-10       Impact factor: 6.005

Review 3.  Recent advances in the Friedländer reaction.

Authors:  José Marco-Contelles; Elena Pérez-Mayoral; Abdelouahid Samadi; María do Carmo Carreiras; Elena Soriano
Journal:  Chem Rev       Date:  2009-06       Impact factor: 60.622

4.  Brønsted acid-catalyzed decarboxylative redox amination: formation of N-alkylindoles from azomethine ylides by isomerization.

Authors:  Hui Mao; Sichang Wang; Peng Yu; Huiqing Lv; Runsheng Xu; Yuanjiang Pan
Journal:  J Org Chem       Date:  2011-01-18       Impact factor: 4.354

5.  Synthetic applications of Pd(II)-catalyzed C-H carboxylation and mechanistic insights: expedient routes to anthranilic acids, oxazolinones, and quinazolinones.

Authors:  Ramesh Giri; Jonathan K Lam; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2010-01-20       Impact factor: 15.419

6.  Structure and total synthesis of (-)-myrionidine and (-)-schoberine, antimalarial alkaloids from Myrioneuron nutans.

Authors:  Van Cuong Pham; Akino Jossang; Philippe Grellier; Thierry Sévenet; Van Hung Nguyen; Bernard Bodo
Journal:  J Org Chem       Date:  2008-09-04       Impact factor: 4.354

7.  Total synthesis of the strychnos alkaloid (+)-minfiensine: tandem enantioselective intramolecular Heck-iminium ion cyclization.

Authors:  Amy B Dounay; Philip G Humphreys; Larry E Overman; Aaron D Wrobleski
Journal:  J Am Chem Soc       Date:  2008-02-28       Impact factor: 15.419

8.  Lewis acid catalyzed formation of tetrahydroquinolines via an intramolecular redox process.

Authors:  Sandip Murarka; Chen Zhang; Marlena D Konieczynska; Daniel Seidel
Journal:  Org Lett       Date:  2009-01-01       Impact factor: 6.005

9.  A flexible synthesis of 2,3-disubstituted indoles from aminobenzyl phosphonium salts. A direct synthesis of rutaecarpine.

Authors:  George A Kraus; Haitao Guo
Journal:  J Org Chem       Date:  2009-08-07       Impact factor: 4.354

10.  Nontraditional reactions of azomethine ylides: decarboxylative three-component couplings of alpha-amino acids.

Authors:  Chen Zhang; Daniel Seidel
Journal:  J Am Chem Soc       Date:  2010-02-17       Impact factor: 15.419
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  12 in total

1.  Redox-Annulations of Cyclic Amines with ortho-Cyanomethylbenzaldehydes.

Authors:  Anirudra Paul; Hemant S Chandak; Longle Ma; Daniel Seidel
Journal:  Org Lett       Date:  2020-01-27       Impact factor: 6.005

2.  Redox-Annulations of Cyclic Amines with Electron-Deficient o-Tolualdehydes.

Authors:  Anirudra Paul; Alafate Adili; Daniel Seidel
Journal:  Org Lett       Date:  2019-03-06       Impact factor: 6.005

3.  The Rügheimer-Burrows reaction revisited: Facile preparation of 4-alkylisoquinolines and 3,5-dialkylpyridines from (partially) saturated amines.

Authors:  Alena Yu Platonova; Daniel Seidel
Journal:  Tetrahedron Lett       Date:  2015-06       Impact factor: 2.415

4.  Condensation-Based Methods for the C-H Bond Functionalization of Amines.

Authors:  Weijie Chen; Daniel Seidel
Journal:  Synthesis (Stuttg)       Date:  2021-09-02       Impact factor: 3.157

5.  Dual C-H functionalization of N-aryl amines: synthesis of polycyclic amines via an oxidative Povarov approach.

Authors:  Chang Min; Abbas Sanchawala; Daniel Seidel
Journal:  Org Lett       Date:  2014-05-01       Impact factor: 6.005

6.  The redox-Mannich reaction.

Authors:  Weijie Chen; Daniel Seidel
Journal:  Org Lett       Date:  2014-05-23       Impact factor: 6.005

7.  Intramolecular [3 + 2]-cycloadditions of azomethine ylides derived from secondary amines via redox-neutral C-H functionalization.

Authors:  Kempegowda Mantelingu; Yingfu Lin; Daniel Seidel
Journal:  Org Lett       Date:  2014-11-03       Impact factor: 6.005

8.  Redox-neutral α-oxygenation of amines: reaction development and elucidation of the mechanism.

Authors:  Matthew T Richers; Martin Breugst; Alena Yu Platonova; Anja Ullrich; Arne Dieckmann; K N Houk; Daniel Seidel
Journal:  J Am Chem Soc       Date:  2014-04-14       Impact factor: 15.419

Review 9.  The azomethine ylide route to amine C-H functionalization: redox-versions of classic reactions and a pathway to new transformations.

Authors:  Daniel Seidel
Journal:  Acc Chem Res       Date:  2015-01-06       Impact factor: 22.384

10.  Redox-neutral α-sulfenylation of secondary amines: ring-fused N,S-acetals.

Authors:  Claire L Jarvis; Matthew T Richers; Martin Breugst; K N Houk; Daniel Seidel
Journal:  Org Lett       Date:  2014-06-13       Impact factor: 6.005
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