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

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

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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

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10.1021/acs.joc.9b02269

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

CCDC 1940217: Experimental Crystal Structure Determination
Bera, T. (Contributor), Singh, B. (Contributor), Hamlin, T. A. (Contributor), Sahoo, S. C. (Contributor) & Saha, J. (Contributor), Unknown Publisher, 1 Jan 2021
DOI: 10.5517/ccdc.csd.cc233ynv, https://doi.org/10.5517%2Fccdc.csd.cc233ynv
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@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.; Sahoo, Subash C.; Saha, Jaideep.

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.

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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

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CCDC 1940217: Experimental Crystal Structure Determination

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