A Method for the Preparation of β‑Amino-α,β-unsaturated Carbonyl Compounds: Study of Solvent Effect and Mechanism

An efficient method for the preparation of β-amino-α,β-unsaturated carbonyl compounds is demonstrated. Bench-stable sodium 3-oxo-enolates were prepared from carbonyl compounds, and reacted with amines in the presence of an acid and a desiccant. DFT studies revealed contrasting mechanisms toward the...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2020-02, Vol.22 (3), p.1040-1045
Main Authors: R. S, Reyno, Sugunan, Akash, S, Ranganayakulu, Suresh, Cherumuttathu H, Rajendar, Goreti
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-a345t-6e91693cf3f13cf132408fa62a4dfd1b044b9f9cead358ab67d79007f6b479503
cites cdi_FETCH-LOGICAL-a345t-6e91693cf3f13cf132408fa62a4dfd1b044b9f9cead358ab67d79007f6b479503
container_end_page 1045
container_issue 3
container_start_page 1040
container_title Organic letters
container_volume 22
creator R. S, Reyno
Sugunan, Akash
S, Ranganayakulu
Suresh, Cherumuttathu H
Rajendar, Goreti
description An efficient method for the preparation of β-amino-α,β-unsaturated carbonyl compounds is demonstrated. Bench-stable sodium 3-oxo-enolates were prepared from carbonyl compounds, and reacted with amines in the presence of an acid and a desiccant. DFT studies revealed contrasting mechanisms toward the reactivity of aliphatic amines in protic solvents and aromatic amines in aprotic solvents. While the former proceeds through the formation of an imine, the latter passes through the Michael addition–elimination mechanism.
doi_str_mv 10.1021/acs.orglett.9b04531
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2347506752</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2347506752</sourcerecordid><originalsourceid>FETCH-LOGICAL-a345t-6e91693cf3f13cf132408fa62a4dfd1b044b9f9cead358ab67d79007f6b479503</originalsourceid><addsrcrecordid>eNp9kE1OwzAQhS0EoqVwAiTkJQvS2nF-anZVVH6kIpAK68iJbZoqsYvtVOqOK3AUepAegpPgqqVLNjOj0XvzNB8Alxj1MQrxgJW2r817LZzr0wJFMcFHoIvjkAQpisPjw5ygDjizdo4Q9ht6CjoEU4owTbtgOYJPws00h1Ib6GYCvhixYIa5SiuoJdysfz6_Rk2ldLD5vtmsg1ZZ5lovEBxmzBRarWqY6WahW8XtLZy6lq-2zqmul0I5OJZSlA4yxX1UOWOqss05OJGstuJi33vg7W78mj0Ek-f7x2w0CRiJYhckguKEklISiX3FJIzQULIkZBGXHPuno4JKWgrGSTxkRZLylCKUyqSIUhoj0gPXu7sLoz9aYV3eVLYUdc2U0K3NQxKlMUpSD6oHyE5aGm2tETJfmKphZpVjlG-B5x54vgee74F719U-oC0awQ-eP8JeMNgJtu65bo3y__578he8lJMl</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2347506752</pqid></control><display><type>article</type><title>A Method for the Preparation of β‑Amino-α,β-unsaturated Carbonyl Compounds: Study of Solvent Effect and Mechanism</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>R. S, Reyno ; Sugunan, Akash ; S, Ranganayakulu ; Suresh, Cherumuttathu H ; Rajendar, Goreti</creator><creatorcontrib>R. S, Reyno ; Sugunan, Akash ; S, Ranganayakulu ; Suresh, Cherumuttathu H ; Rajendar, Goreti</creatorcontrib><description>An efficient method for the preparation of β-amino-α,β-unsaturated carbonyl compounds is demonstrated. Bench-stable sodium 3-oxo-enolates were prepared from carbonyl compounds, and reacted with amines in the presence of an acid and a desiccant. DFT studies revealed contrasting mechanisms toward the reactivity of aliphatic amines in protic solvents and aromatic amines in aprotic solvents. While the former proceeds through the formation of an imine, the latter passes through the Michael addition–elimination mechanism.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.9b04531</identifier><identifier>PMID: 31990197</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Organic letters, 2020-02, Vol.22 (3), p.1040-1045</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a345t-6e91693cf3f13cf132408fa62a4dfd1b044b9f9cead358ab67d79007f6b479503</citedby><cites>FETCH-LOGICAL-a345t-6e91693cf3f13cf132408fa62a4dfd1b044b9f9cead358ab67d79007f6b479503</cites><orcidid>0000-0001-7237-6638 ; 0000-0003-3742-319X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31990197$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>R. S, Reyno</creatorcontrib><creatorcontrib>Sugunan, Akash</creatorcontrib><creatorcontrib>S, Ranganayakulu</creatorcontrib><creatorcontrib>Suresh, Cherumuttathu H</creatorcontrib><creatorcontrib>Rajendar, Goreti</creatorcontrib><title>A Method for the Preparation of β‑Amino-α,β-unsaturated Carbonyl Compounds: Study of Solvent Effect and Mechanism</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>An efficient method for the preparation of β-amino-α,β-unsaturated carbonyl compounds is demonstrated. Bench-stable sodium 3-oxo-enolates were prepared from carbonyl compounds, and reacted with amines in the presence of an acid and a desiccant. DFT studies revealed contrasting mechanisms toward the reactivity of aliphatic amines in protic solvents and aromatic amines in aprotic solvents. While the former proceeds through the formation of an imine, the latter passes through the Michael addition–elimination mechanism.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp9kE1OwzAQhS0EoqVwAiTkJQvS2nF-anZVVH6kIpAK68iJbZoqsYvtVOqOK3AUepAegpPgqqVLNjOj0XvzNB8Alxj1MQrxgJW2r817LZzr0wJFMcFHoIvjkAQpisPjw5ygDjizdo4Q9ht6CjoEU4owTbtgOYJPws00h1Ib6GYCvhixYIa5SiuoJdysfz6_Rk2ldLD5vtmsg1ZZ5lovEBxmzBRarWqY6WahW8XtLZy6lq-2zqmul0I5OJZSlA4yxX1UOWOqss05OJGstuJi33vg7W78mj0Ek-f7x2w0CRiJYhckguKEklISiX3FJIzQULIkZBGXHPuno4JKWgrGSTxkRZLylCKUyqSIUhoj0gPXu7sLoz9aYV3eVLYUdc2U0K3NQxKlMUpSD6oHyE5aGm2tETJfmKphZpVjlG-B5x54vgee74F719U-oC0awQ-eP8JeMNgJtu65bo3y__578he8lJMl</recordid><startdate>20200207</startdate><enddate>20200207</enddate><creator>R. S, Reyno</creator><creator>Sugunan, Akash</creator><creator>S, Ranganayakulu</creator><creator>Suresh, Cherumuttathu H</creator><creator>Rajendar, Goreti</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-7237-6638</orcidid><orcidid>https://orcid.org/0000-0003-3742-319X</orcidid></search><sort><creationdate>20200207</creationdate><title>A Method for the Preparation of β‑Amino-α,β-unsaturated Carbonyl Compounds: Study of Solvent Effect and Mechanism</title><author>R. S, Reyno ; Sugunan, Akash ; S, Ranganayakulu ; Suresh, Cherumuttathu H ; Rajendar, Goreti</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a345t-6e91693cf3f13cf132408fa62a4dfd1b044b9f9cead358ab67d79007f6b479503</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>R. S, Reyno</creatorcontrib><creatorcontrib>Sugunan, Akash</creatorcontrib><creatorcontrib>S, Ranganayakulu</creatorcontrib><creatorcontrib>Suresh, Cherumuttathu H</creatorcontrib><creatorcontrib>Rajendar, Goreti</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>R. S, Reyno</au><au>Sugunan, Akash</au><au>S, Ranganayakulu</au><au>Suresh, Cherumuttathu H</au><au>Rajendar, Goreti</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Method for the Preparation of β‑Amino-α,β-unsaturated Carbonyl Compounds: Study of Solvent Effect and Mechanism</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2020-02-07</date><risdate>2020</risdate><volume>22</volume><issue>3</issue><spage>1040</spage><epage>1045</epage><pages>1040-1045</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>An efficient method for the preparation of β-amino-α,β-unsaturated carbonyl compounds is demonstrated. Bench-stable sodium 3-oxo-enolates were prepared from carbonyl compounds, and reacted with amines in the presence of an acid and a desiccant. DFT studies revealed contrasting mechanisms toward the reactivity of aliphatic amines in protic solvents and aromatic amines in aprotic solvents. While the former proceeds through the formation of an imine, the latter passes through the Michael addition–elimination mechanism.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>31990197</pmid><doi>10.1021/acs.orglett.9b04531</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0001-7237-6638</orcidid><orcidid>https://orcid.org/0000-0003-3742-319X</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2020-02, Vol.22 (3), p.1040-1045
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_2347506752
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
title A Method for the Preparation of β‑Amino-α,β-unsaturated Carbonyl Compounds: Study of Solvent Effect and Mechanism
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-07T13%3A20%3A48IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=A%20Method%20for%20the%20Preparation%20of%20%CE%B2%E2%80%91Amino-%CE%B1,%CE%B2-unsaturated%20Carbonyl%20Compounds:%20Study%20of%20Solvent%20Effect%20and%20Mechanism&rft.jtitle=Organic%20letters&rft.au=R.%20S,%20Reyno&rft.date=2020-02-07&rft.volume=22&rft.issue=3&rft.spage=1040&rft.epage=1045&rft.pages=1040-1045&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.9b04531&rft_dat=%3Cproquest_cross%3E2347506752%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a345t-6e91693cf3f13cf132408fa62a4dfd1b044b9f9cead358ab67d79007f6b479503%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2347506752&rft_id=info:pmid/31990197&rfr_iscdi=true