An effective one-pot access to polynuclear dispiroheterocyclic structures comprising pyrrolidinyloxindole and imidazothiazolotriazine moieties via a 1,3-dipolar cycloaddition strategy

An effective and highly regio- and diastereoselective one-pot method for the synthesis of new polynuclear dispiroheterocyclic systems with five stereogenic centers (dispiro[imidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazine-6,3′-pyrrolidine-2′,3′′-indoles]) comprising pyrrolidinyloxindole and imidazo[4,5-...

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Autores principales: Izmest’ev, Alexei N, Gazieva, Galina A, Sigay, Natalya V, Serkov, Sergei A, Karnoukhova, Valentina A, Kachala, Vadim V, Shashkov, Alexander S, Zanin, Igor E, Kravchenko, Angelina N, Makhova, Nina N
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2016
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5238633/
https://www.ncbi.nlm.nih.gov/pubmed/28144290
http://dx.doi.org/10.3762/bjoc.12.216
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author Izmest’ev, Alexei N
Gazieva, Galina A
Sigay, Natalya V
Serkov, Sergei A
Karnoukhova, Valentina A
Kachala, Vadim V
Shashkov, Alexander S
Zanin, Igor E
Kravchenko, Angelina N
Makhova, Nina N
author_facet Izmest’ev, Alexei N
Gazieva, Galina A
Sigay, Natalya V
Serkov, Sergei A
Karnoukhova, Valentina A
Kachala, Vadim V
Shashkov, Alexander S
Zanin, Igor E
Kravchenko, Angelina N
Makhova, Nina N
author_sort Izmest’ev, Alexei N
collection PubMed
description An effective and highly regio- and diastereoselective one-pot method for the synthesis of new polynuclear dispiroheterocyclic systems with five stereogenic centers (dispiro[imidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazine-6,3′-pyrrolidine-2′,3′′-indoles]) comprising pyrrolidinyloxindole and imidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazine moieties has been developed. The method relies on a 1,3-dipolar cycloaddition of azomethine ylides generated in situ from isatin derivatives and sarcosine to 6-benzylideneimidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazine-2,7-diones.
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spelling pubmed-52386332017-01-31 An effective one-pot access to polynuclear dispiroheterocyclic structures comprising pyrrolidinyloxindole and imidazothiazolotriazine moieties via a 1,3-dipolar cycloaddition strategy Izmest’ev, Alexei N Gazieva, Galina A Sigay, Natalya V Serkov, Sergei A Karnoukhova, Valentina A Kachala, Vadim V Shashkov, Alexander S Zanin, Igor E Kravchenko, Angelina N Makhova, Nina N Beilstein J Org Chem Full Research Paper An effective and highly regio- and diastereoselective one-pot method for the synthesis of new polynuclear dispiroheterocyclic systems with five stereogenic centers (dispiro[imidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazine-6,3′-pyrrolidine-2′,3′′-indoles]) comprising pyrrolidinyloxindole and imidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazine moieties has been developed. The method relies on a 1,3-dipolar cycloaddition of azomethine ylides generated in situ from isatin derivatives and sarcosine to 6-benzylideneimidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazine-2,7-diones. Beilstein-Institut 2016-10-24 /pmc/articles/PMC5238633/ /pubmed/28144290 http://dx.doi.org/10.3762/bjoc.12.216 Text en Copyright © 2016, Izmest’ev et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Izmest’ev, Alexei N
Gazieva, Galina A
Sigay, Natalya V
Serkov, Sergei A
Karnoukhova, Valentina A
Kachala, Vadim V
Shashkov, Alexander S
Zanin, Igor E
Kravchenko, Angelina N
Makhova, Nina N
An effective one-pot access to polynuclear dispiroheterocyclic structures comprising pyrrolidinyloxindole and imidazothiazolotriazine moieties via a 1,3-dipolar cycloaddition strategy
title An effective one-pot access to polynuclear dispiroheterocyclic structures comprising pyrrolidinyloxindole and imidazothiazolotriazine moieties via a 1,3-dipolar cycloaddition strategy
title_full An effective one-pot access to polynuclear dispiroheterocyclic structures comprising pyrrolidinyloxindole and imidazothiazolotriazine moieties via a 1,3-dipolar cycloaddition strategy
title_fullStr An effective one-pot access to polynuclear dispiroheterocyclic structures comprising pyrrolidinyloxindole and imidazothiazolotriazine moieties via a 1,3-dipolar cycloaddition strategy
title_full_unstemmed An effective one-pot access to polynuclear dispiroheterocyclic structures comprising pyrrolidinyloxindole and imidazothiazolotriazine moieties via a 1,3-dipolar cycloaddition strategy
title_short An effective one-pot access to polynuclear dispiroheterocyclic structures comprising pyrrolidinyloxindole and imidazothiazolotriazine moieties via a 1,3-dipolar cycloaddition strategy
title_sort effective one-pot access to polynuclear dispiroheterocyclic structures comprising pyrrolidinyloxindole and imidazothiazolotriazine moieties via a 1,3-dipolar cycloaddition strategy
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5238633/
https://www.ncbi.nlm.nih.gov/pubmed/28144290
http://dx.doi.org/10.3762/bjoc.12.216
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