Organic Letters

, volume 26 , issue 44 , pages 9558-9563

Aza-ortho-Quinone Methide Promoted Strain-Release-Driven Conversion of Azabicyclo[1.1.0]butanes into Functionalized Azetidines

Bandana Singh ¹

Pujan Sasmal ²

Aaron Taites ²

Subhadeep Hazra ²

Jaideep Saha ²

Hide authors affiliations Show authors affiliations: 2 affiliations

Department of Biological and Synthetic Chemistry, Centre of Biomedical Research, Lucknow 226014, India |

Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Mohali 160062, India |

Publication type: Journal Article

Publication date: 2024-10-25

American Chemical Society (ACS)

Organic Letters

scimago Q1

wos Q1

SJR: 1.235

CiteScore: 8.7

Impact factor: 5.0

ISSN: 15237060, 15237052

DOI: 10.1021/acs.orglett.4c03577

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PubMed ID: 39453833

Abstract

A strategy for activating azabicyclo[1.1.0]butane (ABB) with in situ generated aza-ortho-quinone methide, promoted by HFIP, is reported. This unified activation, vis-à-vis strain-release-driven N/C3-functionalization, features a new means to prepare functionalized azetidines from ABB. Additionally, the newly installed motif on azetidine nitrogen could be forged into an indoline via Pd-catalyzed hydroamination, leveraging access to medicinally relevant scaffolds.

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GOST Copy

Singh B. et al. Aza-ortho-Quinone Methide Promoted Strain-Release-Driven Conversion of Azabicyclo[1.1.0]butanes into Functionalized Azetidines // Organic Letters. 2024. Vol. 26. No. 44. pp. 9558-9563.

GOST all authors (up to 50) Copy

Singh B., Sasmal P., Taites A., Hazra S., Saha J. Aza-ortho-Quinone Methide Promoted Strain-Release-Driven Conversion of Azabicyclo[1.1.0]butanes into Functionalized Azetidines // Organic Letters. 2024. Vol. 26. No. 44. pp. 9558-9563.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1021/acs.orglett.4c03577

UR - https://pubs.acs.org/doi/10.1021/acs.orglett.4c03577

TI - Aza-ortho-Quinone Methide Promoted Strain-Release-Driven Conversion of Azabicyclo[1.1.0]butanes into Functionalized Azetidines

T2 - Organic Letters

AU - Singh, Bandana

AU - Sasmal, Pujan

AU - Taites, Aaron

AU - Hazra, Subhadeep

AU - Saha, Jaideep

PY - 2024

DA - 2024/10/25

PB - American Chemical Society (ACS)

SP - 9558-9563

IS - 44

VL - 26

PMID - 39453833

SN - 1523-7060

SN - 1523-7052

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2024_Singh,

author = {Bandana Singh and Pujan Sasmal and Aaron Taites and Subhadeep Hazra and Jaideep Saha},

title = {Aza-ortho-Quinone Methide Promoted Strain-Release-Driven Conversion of Azabicyclo[1.1.0]butanes into Functionalized Azetidines},

journal = {Organic Letters},

year = {2024},

volume = {26},

publisher = {American Chemical Society (ACS)},

month = {oct},

url = {https://pubs.acs.org/doi/10.1021/acs.orglett.4c03577},

number = {44},

pages = {9558--9563},

doi = {10.1021/acs.orglett.4c03577}

}

MLA

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MLA Copy

Singh, Bandana, et al. “Aza-ortho-Quinone Methide Promoted Strain-Release-Driven Conversion of Azabicyclo[1.1.0]butanes into Functionalized Azetidines.” Organic Letters, vol. 26, no. 44, Oct. 2024, pp. 9558-9563. https://pubs.acs.org/doi/10.1021/acs.orglett.4c03577.

Publisher

American Chemical Society (ACS)

Journal

Organic Letters

scimago Q1

wos Q1

SJR

1.235

CiteScore

8.7

Impact factor

5.0

ISSN

15237060 (Print)

15237052 (Electronic)