Cargando…

Substrate-Controlled Diversity-Oriented Synthesis of Novel Polycyclic Frameworks via [4 + 2] and [3 + 2] Annulations of Ninhydrin-Derived MBH Adducts with 3,4-Dihydroisoquinolines

Substrate-controlled diversity-oriented synthesis of polycyclic frameworks via [4 + 2] and [3 + 2] annulations between ninhydrin-derived Morita–Baylis–Hillman (MBH) adducts and 3,4-dihydroisoquinolines under similar reaction conditions have been developed. The reaction provides diversity-oriented sy...

Descripción completa

Detalles Bibliográficos
Autores principales: Wang, Kaikai, Zhou, Wenwen, Jia, Jun, Ye, Junwei, Yuan, Mengxin, Yang, Jie, Qi, Yonghua, Chen, Rongxiang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10574269/
https://www.ncbi.nlm.nih.gov/pubmed/37836604
http://dx.doi.org/10.3390/molecules28196761
_version_ 1785120654317584384
author Wang, Kaikai
Zhou, Wenwen
Jia, Jun
Ye, Junwei
Yuan, Mengxin
Yang, Jie
Qi, Yonghua
Chen, Rongxiang
author_facet Wang, Kaikai
Zhou, Wenwen
Jia, Jun
Ye, Junwei
Yuan, Mengxin
Yang, Jie
Qi, Yonghua
Chen, Rongxiang
author_sort Wang, Kaikai
collection PubMed
description Substrate-controlled diversity-oriented synthesis of polycyclic frameworks via [4 + 2] and [3 + 2] annulations between ninhydrin-derived Morita–Baylis–Hillman (MBH) adducts and 3,4-dihydroisoquinolines under similar reaction conditions have been developed. The reaction provides diversity-oriented synthesis of a series of novel and structurally complex spiro multi heterocyclic skeletons in good yields (up to 87% and 90%, respectively) with excellent diastereoselectivities (up to >25:1 dr). In particular, the switchable [4 + 2] and [3 + 2] annulation reactions are controlled by tuning the hydroxyl protecting group on the ninhydrin-derived MBH adduct to deliver structural diverse spiro[indene-2,2′-[1,3]oxazino[2,3-a]isoquinoline] and spiro[indene-2,1′-pyrrolo[2,1-a]isoquinoline], respectively. Furthermore, the relative configuration and chemical structure of two kinds of cycloadducts were confirmed through X-ray diffraction analysis.
format Online
Article
Text
id pubmed-10574269
institution National Center for Biotechnology Information
language English
publishDate 2023
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-105742692023-10-14 Substrate-Controlled Diversity-Oriented Synthesis of Novel Polycyclic Frameworks via [4 + 2] and [3 + 2] Annulations of Ninhydrin-Derived MBH Adducts with 3,4-Dihydroisoquinolines Wang, Kaikai Zhou, Wenwen Jia, Jun Ye, Junwei Yuan, Mengxin Yang, Jie Qi, Yonghua Chen, Rongxiang Molecules Article Substrate-controlled diversity-oriented synthesis of polycyclic frameworks via [4 + 2] and [3 + 2] annulations between ninhydrin-derived Morita–Baylis–Hillman (MBH) adducts and 3,4-dihydroisoquinolines under similar reaction conditions have been developed. The reaction provides diversity-oriented synthesis of a series of novel and structurally complex spiro multi heterocyclic skeletons in good yields (up to 87% and 90%, respectively) with excellent diastereoselectivities (up to >25:1 dr). In particular, the switchable [4 + 2] and [3 + 2] annulation reactions are controlled by tuning the hydroxyl protecting group on the ninhydrin-derived MBH adduct to deliver structural diverse spiro[indene-2,2′-[1,3]oxazino[2,3-a]isoquinoline] and spiro[indene-2,1′-pyrrolo[2,1-a]isoquinoline], respectively. Furthermore, the relative configuration and chemical structure of two kinds of cycloadducts were confirmed through X-ray diffraction analysis. MDPI 2023-09-22 /pmc/articles/PMC10574269/ /pubmed/37836604 http://dx.doi.org/10.3390/molecules28196761 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Wang, Kaikai
Zhou, Wenwen
Jia, Jun
Ye, Junwei
Yuan, Mengxin
Yang, Jie
Qi, Yonghua
Chen, Rongxiang
Substrate-Controlled Diversity-Oriented Synthesis of Novel Polycyclic Frameworks via [4 + 2] and [3 + 2] Annulations of Ninhydrin-Derived MBH Adducts with 3,4-Dihydroisoquinolines
title Substrate-Controlled Diversity-Oriented Synthesis of Novel Polycyclic Frameworks via [4 + 2] and [3 + 2] Annulations of Ninhydrin-Derived MBH Adducts with 3,4-Dihydroisoquinolines
title_full Substrate-Controlled Diversity-Oriented Synthesis of Novel Polycyclic Frameworks via [4 + 2] and [3 + 2] Annulations of Ninhydrin-Derived MBH Adducts with 3,4-Dihydroisoquinolines
title_fullStr Substrate-Controlled Diversity-Oriented Synthesis of Novel Polycyclic Frameworks via [4 + 2] and [3 + 2] Annulations of Ninhydrin-Derived MBH Adducts with 3,4-Dihydroisoquinolines
title_full_unstemmed Substrate-Controlled Diversity-Oriented Synthesis of Novel Polycyclic Frameworks via [4 + 2] and [3 + 2] Annulations of Ninhydrin-Derived MBH Adducts with 3,4-Dihydroisoquinolines
title_short Substrate-Controlled Diversity-Oriented Synthesis of Novel Polycyclic Frameworks via [4 + 2] and [3 + 2] Annulations of Ninhydrin-Derived MBH Adducts with 3,4-Dihydroisoquinolines
title_sort substrate-controlled diversity-oriented synthesis of novel polycyclic frameworks via [4 + 2] and [3 + 2] annulations of ninhydrin-derived mbh adducts with 3,4-dihydroisoquinolines
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10574269/
https://www.ncbi.nlm.nih.gov/pubmed/37836604
http://dx.doi.org/10.3390/molecules28196761
work_keys_str_mv AT wangkaikai substratecontrolleddiversityorientedsynthesisofnovelpolycyclicframeworksvia42and32annulationsofninhydrinderivedmbhadductswith34dihydroisoquinolines
AT zhouwenwen substratecontrolleddiversityorientedsynthesisofnovelpolycyclicframeworksvia42and32annulationsofninhydrinderivedmbhadductswith34dihydroisoquinolines
AT jiajun substratecontrolleddiversityorientedsynthesisofnovelpolycyclicframeworksvia42and32annulationsofninhydrinderivedmbhadductswith34dihydroisoquinolines
AT yejunwei substratecontrolleddiversityorientedsynthesisofnovelpolycyclicframeworksvia42and32annulationsofninhydrinderivedmbhadductswith34dihydroisoquinolines
AT yuanmengxin substratecontrolleddiversityorientedsynthesisofnovelpolycyclicframeworksvia42and32annulationsofninhydrinderivedmbhadductswith34dihydroisoquinolines
AT yangjie substratecontrolleddiversityorientedsynthesisofnovelpolycyclicframeworksvia42and32annulationsofninhydrinderivedmbhadductswith34dihydroisoquinolines
AT qiyonghua substratecontrolleddiversityorientedsynthesisofnovelpolycyclicframeworksvia42and32annulationsofninhydrinderivedmbhadductswith34dihydroisoquinolines
AT chenrongxiang substratecontrolleddiversityorientedsynthesisofnovelpolycyclicframeworksvia42and32annulationsofninhydrinderivedmbhadductswith34dihydroisoquinolines