Literature DB >> 32602717

Synthesis of Pyrrolopyrazinones by Construction of the Pyrrole Ring onto an Intact Diketopiperazine.

Susanna K Maisto1, Angela P Leersnyder1, Gwyneth L Pudner1, Jonathan R Scheerer1.   

Abstract

This study reveals an alternative sequence for the synthesis of compounds that contain the pyrrolodiketopiperazine structural motif. Starting with a diketopiperazine precursor, a mild aldol condensation precedes pyrrole annulation and bicyclic ring fusion. The derived intermediate aldol condensation products, which bear either a protected carbonyl or a functionalized alkyne, can be cyclized to the pyrrolodiketopiperazine by protic or gold Lewis acid catalysis.

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Year:  2020        PMID： 32602717      PMCID： PMC7464856          DOI： 10.1021/acs.joc.0c01263

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  33 in total

Review 1.  Pyrrole, pyrrolidine, pyridine, piperidine and tropane alkaloids.

Authors:  D O'Hagan
Journal:  Nat Prod Rep       Date:  2000-10       Impact factor: 13.423

Review 2.  2,5-Diketopiperazines: synthesis, reactions, medicinal chemistry, and bioactive natural products.

Authors:  Alan D Borthwick
Journal:  Chem Rev       Date:  2012-05-11       Impact factor: 60.622

3.  Gold-catalyzed carbon-heteroatom bond-forming reactions.

Authors:  A Corma; A Leyva-Pérez; Maria J Sabater
Journal:  Chem Rev       Date:  2011-03-09       Impact factor: 60.622

4.  Domino approach for the synthesis of pyrrolo[1,2-alpha]pyrazine from vinyl azides.

Authors:  Wenteng Chen; Miao Hu; Jianwei Wu; Hongbin Zou; Yongping Yu
Journal:  Org Lett       Date:  2010-09-03       Impact factor: 6.005

5.  A practical preparation of highly versatile N-acylpyrroles from 2,4,4-trimethoxybutan-1-amine.

Authors:  Tomoaki Maehara; Rentaro Kanno; Satoshi Yokoshima; Tohru Fukuyama
Journal:  Org Lett       Date:  2012-03-26       Impact factor: 6.005

6.  Asymmetric aziridination of cyclic enones using chiral diamine catalysts and its application to the total synthesis of (-)-agelastatin A.

Authors:  Yasuhiro Menjo; Akinari Hamajima; Neri Sasaki; Yasumasa Hamada
Journal:  Org Lett       Date:  2011-10-03       Impact factor: 6.005

7.  Asymmetric annulation toward pyrrolopiperazinones: concise enantioselective syntheses of pyrrole alkaloid natural products.

Authors:  Barry M Trost; Guangbin Dong
Journal:  Org Lett       Date:  2007-05-12       Impact factor: 6.005

8.  Synthesis of monoalkylidene diketopiperazines and application to the synthesis of barettin.

Authors:  Elizabeth W Kelley; Skylar G Norman; Jonathan R Scheerer
Journal:  Org Biomol Chem       Date:  2017-10-18       Impact factor: 3.876

9.  Synthesis and SAR of novel tricyclic quinoxalinone inhibitors of poly(ADP-ribose)polymerase-1 (PARP-1).

Authors:  Julie Miyashiro; Keith W Woods; Chang H Park; Xuesong Liu; Yan Shi; Eric F Johnson; Jennifer J Bouska; Amanda M Olson; Yan Luo; Elizabeth H Fry; Vincent L Giranda; Thomas D Penning
Journal:  Bioorg Med Chem Lett       Date:  2009-06-13       Impact factor: 2.823

10.  Nucleophilic and electrophilic cyclization of N-alkyne-substituted pyrrole derivatives: Synthesis of pyrrolopyrazinone, pyrrolotriazinone, and pyrrolooxazinone moieties.

Authors:  Işıl Yenice; Sinan Basceken; Metin Balci
Journal:  Beilstein J Org Chem       Date:  2017-05-04       Impact factor: 2.883
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  1 in total

Review 1.  Diketopiperazine Gels: New Horizons from the Self-Assembly of Cyclic Dipeptides.

Authors:  Marco Scarel; Silvia Marchesan
Journal:  Molecules       Date:  2021-06-03       Impact factor: 4.411
  1 in total

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