Literature DB >> 34054152

A cascade reaction of cinnamyl azides with vinyl sulfones directly generates dihydro-pyrrolo-pyrazole heterocycles.

Angela S Carlson1, Alexandru M Petre1, Joseph J Topczewski1.   

Abstract

This report describes the direct synthesis of dihydro-pyrrolo-pyrazole heterocycles from allylic azides and methyl vinyl sulfone. The product results from a complex cascade reaction that is operationally straightforward, with aromatization being the result of a concomitant elimination step. A variety of azides could participate in this reaction (12 examples) and the isolated yields of the desired product ranged from 51%-72%. Lastly the ethylene sulfone group could be removed by heating the product in pyrrolidine.

Entities:  

Keywords:  Azide; Cascade reaction; Pyrazole; Pyrrolidine; Vinyl sulfone

Year:  2021        PMID： 34054152      PMCID： PMC8153508          DOI： 10.1016/j.tetlet.2021.152860

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  12 in total

1.  Observations on the reaction of hydrazones with iodine: interception of the diazo intermediates.

Authors:  Béatrice Quiclet-Sire; Samir Z Zard
Journal:  Chem Commun (Camb)       Date:  2006-03-30       Impact factor: 6.222

2.  Design and Synthesis of Novel and Selective Glycine Transporter-1 (GlyT1) Inhibitors with Memory Enhancing Properties.

Authors:  Vincent J Santora; Theresa A Almos; Richard Barido; Jillian Basinger; Chris L Bellows; Brett C Bookser; J Guy Breitenbucher; Nicola J Broadbent; Clifford Cabebe; Chih-Kun Chai; Mi Chen; Stephine Chow; De Michael Chung; Lindsay Crickard; Anne M Danks; Graeme C Freestone; Dany Gitnick; Varsha Gupta; Christine Hoffmaster; Andrew R Hudson; Alan P Kaplan; Michael R Kennedy; Dong Lee; James Limberis; Kiev Ly; Chi Ching Mak; Brittany Masatsugu; Andrew C Morse; Jim Na; David Neul; John Nikpur; Marco Peters; Robert E Petroski; Joel Renick; Kristen Sebring; Samantha Sevidal; Ali Tabatabaei; Jenny Wen; Yingzhuo Yan; Zachary W Yoder; Douglas Zook
Journal:  J Med Chem       Date:  2018-07-11       Impact factor: 7.446

Review 3.  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

4.  2,4-Diamino-8-quinazoline carboxamides as novel, potent inhibitors of the NAD hydrolyzing enzyme CD38: Exploration of the 2-position structure-activity relationships.

Authors:  David N Deaton; Curt D Haffner; Brad R Henke; Michael R Jeune; Barry G Shearer; Eugene L Stewart; J Darren Stuart; John C Ulrich
Journal:  Bioorg Med Chem       Date:  2018-03-15       Impact factor: 3.641

5.  1,3-Dipolar cycloaddition reactivities of perfluorinated aryl azides with enamines and strained dipolarophiles.

Authors:  Sheng Xie; Steven A Lopez; Olof Ramström; Mingdi Yan; K N Houk
Journal:  J Am Chem Soc       Date:  2015-02-18       Impact factor: 15.419

6.  A phase I study of danusertib (PHA-739358) in adult patients with accelerated or blastic phase chronic myeloid leukemia and Philadelphia chromosome-positive acute lymphoblastic leukemia resistant or intolerant to imatinib and/or other second generation c-ABL therapy.

Authors:  Gautam Borthakur; Herve Dombret; Philippe Schafhausen; Tim Henrik Brummendorf; Nicolas Boissel; Elias Jabbour; Mariangela Mariani; Laura Capolongo; Patrizia Carpinelli; Cristina Davite; Hagop Kantarjian; Jorge E Cortes
Journal:  Haematologica       Date:  2015-04-17       Impact factor: 9.941

7.  1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazoles: identification of a potent Aurora kinase inhibitor with a favorable antitumor kinase inhibition profile.

Authors:  Daniele Fancelli; Jürgen Moll; Mario Varasi; Rodrigo Bravo; Roberta Artico; Daniela Berta; Simona Bindi; Alexander Cameron; Ilaria Candiani; Paolo Cappella; Patrizia Carpinelli; Walter Croci; Barbara Forte; Maria Laura Giorgini; Jan Klapwijk; Aurelio Marsiglio; Enrico Pesenti; Maurizio Rocchetti; Fulvia Roletto; Dino Severino; Chiara Soncini; Paola Storici; Roberto Tonani; Paola Zugnoni; Paola Vianello
Journal:  J Med Chem       Date:  2006-11-30       Impact factor: 7.446

8.  On the Winstein rearrangement: equilibrium and mechanism.

Authors:  Amy A Ott; Joseph J Topczewski
Journal:  ARKIVOC       Date:  2019-03-30       Impact factor: 1.140

9.  A Cascade Reaction of Cinnamyl Azides with Acrylates Directly Generates Tetrahydro-Pyrrolo-Pyrazole Heterocycles.

Authors:  Angela S Carlson; En-Chih Liu; Joseph J Topczewski
Journal:  J Org Chem       Date:  2020-04-20       Impact factor: 4.354

10.  Secondary Products from Intramolecular Cycloadditions of Azidoalkyl Enol Ethers and Azidoalkyl Vinyl Bromides: 1-Azadienes, Their Reactions with Diphenylketene, and Radical Cyclizations To Form Bi- and Tricyclic Lactams.

Authors:  John T R Liddon; Peter J Lindsay-Scott; Jeremy Robertson
Journal:  J Org Chem       Date:  2019-10-03       Impact factor: 4.354
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  1 in total

Review 1.  A Review of the Recent Development in the Synthesis and Biological Evaluations of Pyrazole Derivatives.

Authors:  Oluwakemi Ebenezer; Michael Shapi; Jack A Tuszynski
Journal:  Biomedicines       Date:  2022-05-12
  1 in total

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