One-Step Assembly of Functionalized Morpholinones and 1,4-Oxazepane-3-ones via [3 + 3]- And [3 + 4]-Annulation of Aza-Oxyallyl Cation and Amphoteric Compounds

Tishyasoumya Bera; Bandana Singh; Trevor A. Hamlin; Subash C. Sahoo; Jaideep Saha

doi:10.1021/acs.joc.9b02269

One-Step Assembly of Functionalized Morpholinones and 1,4-Oxazepane-3-ones via [3 + 3]- And [3 + 4]-Annulation of Aza-Oxyallyl Cation and Amphoteric Compounds

Tishyasoumya Bera, Bandana Singh, Trevor A. Hamlin, Subash C. Sahoo, Jaideep Saha^*

^*Corresponding author for this work

AIMMS

Research output: Contribution to Journal › Article › Academic › peer-review

306 Downloads (Pure)

Abstract

A new [3 + 3]- and [3 + 4]-annulation strategy involving azaoxyallyl cation and [1,m]-amphoteric compounds (m = 3,4) is presented. This concise method enables easy assembly of functionalized saturated N-heterocycles, comprised of six-and seven-membered rings and is of high significance in the context of drug discovery approaches. This reaction also represents a new trapping modality of the azaoxyallyl cation with amphoteric agents of different chain lengths that consist of a heteroatom nucleophilic site and a π-electrophilic site.

Original language	English
Pages (from-to)	15255-15266
Number of pages	12
Journal	Journal of Organic Chemistry
Volume	84
Issue number	23
Early online date	8 Nov 2019
DOIs	https://doi.org/10.1021/acs.joc.9b02269
Publication status	Published - 6 Dec 2019

Funding

J.S. thanks SERB, New Delhi (ECR/2016/001474) for funding. T.S.B is an INSPIRE-JRF and B.S. thank CSIR, New Delhi for fellowship. J.S. thanks Director CBMR for research facilities. J.S. sincerely thanks Prof. Andrei Yudin (U Toronto) for some important comments on this work. S.S thanks DST-FIST for the single crystal X-ray facility at Punjab University (P.U), Chandigarh.

Funders	Funder number
INSPIRE-JRF
Council of Scientific and Industrial Research, India
Science and Engineering Research Board	ECR/2016/001474

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Access to Document

10.1021/acs.joc.9b02269

acs.joc.9b02269_OneStep Assembly of Functionalized Morpholinones andFinal published version, 1.18 MBLicence: Article 25fa Dutch Copyright Act

Persistent URL (handle)

Persistent link

Cite this

@article{5cf015746c0f4ec688e2685ff0de6494,

title = "One-Step Assembly of Functionalized Morpholinones and 1,4-Oxazepane-3-ones via [3 + 3]- And [3 + 4]-Annulation of Aza-Oxyallyl Cation and Amphoteric Compounds",

abstract = "A new [3 + 3]- and [3 + 4]-annulation strategy involving azaoxyallyl cation and [1,m]-amphoteric compounds (m = 3,4) is presented. This concise method enables easy assembly of functionalized saturated N-heterocycles, comprised of six-and seven-membered rings and is of high significance in the context of drug discovery approaches. This reaction also represents a new trapping modality of the azaoxyallyl cation with amphoteric agents of different chain lengths that consist of a heteroatom nucleophilic site and a π-electrophilic site.",

author = "Tishyasoumya Bera and Bandana Singh and Hamlin, {Trevor A.} and Sahoo, {Subash C.} and Jaideep Saha",

year = "2019",

month = dec,

day = "6",

doi = "10.1021/acs.joc.9b02269",

language = "English",

volume = "84",

pages = "15255--15266",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "23",

}

One-Step Assembly of Functionalized Morpholinones and 1,4-Oxazepane-3-ones via [3 + 3]- And [3 + 4]-Annulation of Aza-Oxyallyl Cation and Amphoteric Compounds. / Bera, Tishyasoumya; Singh, Bandana; Hamlin, Trevor A. et al.
In: Journal of Organic Chemistry, Vol. 84, No. 23, 06.12.2019, p. 15255-15266.

Research output: Contribution to Journal › Article › Academic › peer-review

TY - JOUR

T1 - One-Step Assembly of Functionalized Morpholinones and 1,4-Oxazepane-3-ones via [3 + 3]- And [3 + 4]-Annulation of Aza-Oxyallyl Cation and Amphoteric Compounds

AU - Bera, Tishyasoumya

AU - Singh, Bandana

AU - Hamlin, Trevor A.

AU - Sahoo, Subash C.

AU - Saha, Jaideep

PY - 2019/12/6

Y1 - 2019/12/6

N2 - A new [3 + 3]- and [3 + 4]-annulation strategy involving azaoxyallyl cation and [1,m]-amphoteric compounds (m = 3,4) is presented. This concise method enables easy assembly of functionalized saturated N-heterocycles, comprised of six-and seven-membered rings and is of high significance in the context of drug discovery approaches. This reaction also represents a new trapping modality of the azaoxyallyl cation with amphoteric agents of different chain lengths that consist of a heteroatom nucleophilic site and a π-electrophilic site.

AB - A new [3 + 3]- and [3 + 4]-annulation strategy involving azaoxyallyl cation and [1,m]-amphoteric compounds (m = 3,4) is presented. This concise method enables easy assembly of functionalized saturated N-heterocycles, comprised of six-and seven-membered rings and is of high significance in the context of drug discovery approaches. This reaction also represents a new trapping modality of the azaoxyallyl cation with amphoteric agents of different chain lengths that consist of a heteroatom nucleophilic site and a π-electrophilic site.

UR - http://www.scopus.com/inward/record.url?scp=85075445480&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85075445480&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.9b02269

DO - 10.1021/acs.joc.9b02269

M3 - Article

C2 - 31702149

AN - SCOPUS:85075445480

SN - 0022-3263

VL - 84

SP - 15255

EP - 15266

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 23

ER -

One-Step Assembly of Functionalized Morpholinones and 1,4-Oxazepane-3-ones via [3 + 3]- And [3 + 4]-Annulation of Aza-Oxyallyl Cation and Amphoteric Compounds

Abstract

Funding

UN SDGs

Access to Document

Persistent URL (handle)

Other files and links

Fingerprint

CCDC 1940217: Experimental Crystal Structure Determination

Cite this

One-Step Assembly of Functionalized Morpholinones and 1,4-Oxazepane-3-ones via [3 + 3]- And [3 + 4]-Annulation of Aza-Oxyallyl Cation and Amphoteric Compounds

Abstract

Funding

UN SDGs

Access to Document

Persistent URL (handle)

Other files and links

Fingerprint

Datasets

CCDC 1940217: Experimental Crystal Structure Determination

Cite this