Dibenzothiazepine Based MCR Chemistry

Xiaofang Lei; Giasemi Angeli; Alexander Dömling; Constantinos G. Neochoritis

doi:10.1002/ejoc.202200220

Dibenzothiazepine Based MCR Chemistry

Xiaofang Lei, Giasemi Angeli, Alexander Dömling, Constantinos G. Neochoritis^*

^*Bijbehorende auteur voor dit werk

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Privileged scaffolds which can unveil unknown territories of the chemical space are constantly prominent. As such, 1,5-dibenzothiazepines not only offer structural diversification but also a very unique binding mode due to their “butterfly” conformation. We provide MCR-based annulations of this scaffold towards three different tetracycles in a straightforward, two-step procedure. We synthesize a library of 30 tetracyclic 1,5-tetrazolo-, fused imidazo- and lactam-1,5-dibenzothiazepines with scalable and one-pot procedures. In addition, we obtained single crystal structures of certain derivatives, demonstrating the conformational behavior of the scaffold.

Originele taal-2	English
Artikelnummer	e202200220
Aantal pagina's	5
Tijdschrift	European Journal of Organic Chemistry
Volume	2022
Nummer van het tijdschrift	20
DOI's	https://doi.org/10.1002/ejoc.202200220
Status	Published - 25-mei-2022

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10.1002/ejoc.202200220

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CCDC 2123182: Experimental Crystal Structure Determination
Lei, X. (Contributor), Angeli, G. (Contributor), Dömling, A. (Contributor) & Neochoritis, C. G. (Contributor), Cambridge Crystallographic Data Centre, 19-nov.-2022
DOI: 10.5517/ccdc.csd.cc298brp
Dataset
CCDC 2123184: Experimental Crystal Structure Determination
Lei, X. (Contributor), Angeli, G. (Contributor), Dömling, A. (Contributor) & Neochoritis, C. G. (Contributor), Cambridge Crystallographic Data Centre, 19-nov.-2022
DOI: 10.5517/ccdc.csd.cc298btr
Dataset
CCDC 2123183: Experimental Crystal Structure Determination
Lei, X. (Contributor), Angeli, G. (Contributor), Dömling, A. (Contributor) & Neochoritis, C. G. (Contributor), Cambridge Crystallographic Data Centre, 19-nov.-2022
DOI: 10.5517/ccdc.csd.cc298bsq
Dataset

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@article{0ad99b8afe5e43f1ac4361e9186dcc73,

title = "Dibenzothiazepine Based MCR Chemistry",

abstract = "Privileged scaffolds which can unveil unknown territories of the chemical space are constantly prominent. As such, 1,5-dibenzothiazepines not only offer structural diversification but also a very unique binding mode due to their “butterfly” conformation. We provide MCR-based annulations of this scaffold towards three different tetracycles in a straightforward, two-step procedure. We synthesize a library of 30 tetracyclic 1,5-tetrazolo-, fused imidazo- and lactam-1,5-dibenzothiazepines with scalable and one-pot procedures. In addition, we obtained single crystal structures of certain derivatives, demonstrating the conformational behavior of the scaffold.",

keywords = "Atropisomerism, Dibenzothiazepines, Multicomponent reactions, Privileged scaffolds, Ugi reaction",

author = "Xiaofang Lei and Giasemi Angeli and Alexander D{\"o}mling and Neochoritis, {Constantinos G.}",

note = "Funding Information: The research project (to C.G.N) was supported by the Hellenic Foundation for Research and Innovation (H.F.R.I.) under the “2 Call for H.F.R.I. Research Projects to support Post‐Doctoral Researchers” (Project Number: 0911) and the University of Crete (UoC‐ELKE). Xiaofang Lei acknowledges the China Scholarship Council for support. nd Publisher Copyright: {\textcopyright} 2022 Wiley-VCH GmbH.",

year = "2022",

month = may,

day = "25",

doi = "10.1002/ejoc.202200220",

language = "English",

volume = "2022",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "WILEY-V C H VERLAG GMBH",

number = "20",

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TY - JOUR

T1 - Dibenzothiazepine Based MCR Chemistry

AU - Lei, Xiaofang

AU - Angeli, Giasemi

AU - Dömling, Alexander

AU - Neochoritis, Constantinos G.

N1 - Funding Information: The research project (to C.G.N) was supported by the Hellenic Foundation for Research and Innovation (H.F.R.I.) under the “2 Call for H.F.R.I. Research Projects to support Post‐Doctoral Researchers” (Project Number: 0911) and the University of Crete (UoC‐ELKE). Xiaofang Lei acknowledges the China Scholarship Council for support. nd Publisher Copyright: © 2022 Wiley-VCH GmbH.

PY - 2022/5/25

Y1 - 2022/5/25

N2 - Privileged scaffolds which can unveil unknown territories of the chemical space are constantly prominent. As such, 1,5-dibenzothiazepines not only offer structural diversification but also a very unique binding mode due to their “butterfly” conformation. We provide MCR-based annulations of this scaffold towards three different tetracycles in a straightforward, two-step procedure. We synthesize a library of 30 tetracyclic 1,5-tetrazolo-, fused imidazo- and lactam-1,5-dibenzothiazepines with scalable and one-pot procedures. In addition, we obtained single crystal structures of certain derivatives, demonstrating the conformational behavior of the scaffold.

AB - Privileged scaffolds which can unveil unknown territories of the chemical space are constantly prominent. As such, 1,5-dibenzothiazepines not only offer structural diversification but also a very unique binding mode due to their “butterfly” conformation. We provide MCR-based annulations of this scaffold towards three different tetracycles in a straightforward, two-step procedure. We synthesize a library of 30 tetracyclic 1,5-tetrazolo-, fused imidazo- and lactam-1,5-dibenzothiazepines with scalable and one-pot procedures. In addition, we obtained single crystal structures of certain derivatives, demonstrating the conformational behavior of the scaffold.

KW - Atropisomerism

KW - Dibenzothiazepines

KW - Multicomponent reactions

KW - Privileged scaffolds

KW - Ugi reaction

UR - http://www.scopus.com/inward/record.url?scp=85130616355&partnerID=8YFLogxK

U2 - 10.1002/ejoc.202200220

DO - 10.1002/ejoc.202200220

M3 - Article

AN - SCOPUS:85130616355

VL - 2022

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 20

M1 - e202200220

ER -

Dibenzothiazepine Based MCR Chemistry

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Datasets

CCDC 2123182: Experimental Crystal Structure Determination

CCDC 2123184: Experimental Crystal Structure Determination

CCDC 2123183: Experimental Crystal Structure Determination

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