Azidophosphonium salt-directed chemoselective synthesis of (E)/(Z)-cinnamyl-1H-triazoles and regiospecific access to bromomethylcoumarins from Morita–Baylis–Hillman adducts

Azidophosphonium salt-directed chemoselective synthesis of (E)/(Z)-cinnamyl-1H-triazoles and regiospecific access to bromomethylcoumarins from Morita–Baylis–Hillman adducts

The direct transformation of Morita–Baylis–Hillman (MBH) adducts into molecules of interest is a crucial process wherein allylic hydroxy-protected or halogenated MBH adducts are commonly preferred. Herein, we report an azidophosphonium salt (AzPS)-catalysed straight forward protocol for synthesising...

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Main Authors: Soundararajan Karthikeyan, Radha Krishnan Shobana, Kamarajapurathu Raju Subimol, J. Helen Ratna Monica, Ayyanoth Karthik Krishna Kumar
Format: Article
Language:English
Published: Beilstein-Institut 2020-07-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
halomethylcoumarin
morita–baylis–hillman adducts
organocatalyst
phosphonium salt
triazolation
Online Access:https://doi.org/10.3762/bjoc.16.130
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spelling doaj-90f3a4a22b5848deb64907eb8ca74fe62021-04-02T09:23:27ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972020-07-011611579158710.3762/bjoc.16.1301860-5397-16-130Azidophosphonium salt-directed chemoselective synthesis of (E)/(Z)-cinnamyl-1H-triazoles and regiospecific access to bromomethylcoumarins from Morita–Baylis–Hillman adductsSoundararajan Karthikeyan0Radha Krishnan Shobana1Kamarajapurathu Raju Subimol2J. Helen Ratna Monica3Ayyanoth Karthik Krishna Kumar4Organic & Material Chemistry Research Laboratory, Department of Chemistry, The American College, Madurai, Tamil Nadu, IndiaOrganic & Material Chemistry Research Laboratory, Department of Chemistry, The American College, Madurai, Tamil Nadu, IndiaDepartment of Chemistry, Fatima College, Madurai, Tamil Nadu, IndiaOrganic & Material Chemistry Research Laboratory, Department of Chemistry, The American College, Madurai, Tamil Nadu, IndiaOrganic & Material Chemistry Research Laboratory, Department of Chemistry, The American College, Madurai, Tamil Nadu, IndiaThe direct transformation of Morita–Baylis–Hillman (MBH) adducts into molecules of interest is a crucial process wherein allylic hydroxy-protected or halogenated MBH adducts are commonly preferred. Herein, we report an azidophosphonium salt (AzPS)-catalysed straight forward protocol for synthesising structurally demanding (E)/(Z)-cinnamyl-1H-1,2,3-triazoles and halomethylcoumarins from MBH adducts. The novel methodology, efficient catalyst, and direct utilization of MBH adducts under mild reaction conditions qualify the reported procedures as powerful synthetic tools.https://doi.org/10.3762/bjoc.16.130halomethylcoumarinmorita–baylis–hillman adductsorganocatalystphosphonium salttriazolation
collection DOAJ
language English
format Article
sources DOAJ
author Soundararajan Karthikeyan
Radha Krishnan Shobana
Kamarajapurathu Raju Subimol
J. Helen Ratna Monica
Ayyanoth Karthik Krishna Kumar
spellingShingle Soundararajan Karthikeyan
Radha Krishnan Shobana
Kamarajapurathu Raju Subimol
J. Helen Ratna Monica
Ayyanoth Karthik Krishna Kumar
Azidophosphonium salt-directed chemoselective synthesis of (E)/(Z)-cinnamyl-1H-triazoles and regiospecific access to bromomethylcoumarins from Morita–Baylis–Hillman adducts
Beilstein Journal of Organic Chemistry
halomethylcoumarin
morita–baylis–hillman adducts
organocatalyst
phosphonium salt
triazolation
author_facet Soundararajan Karthikeyan
Radha Krishnan Shobana
Kamarajapurathu Raju Subimol
J. Helen Ratna Monica
Ayyanoth Karthik Krishna Kumar
author_sort Soundararajan Karthikeyan
title Azidophosphonium salt-directed chemoselective synthesis of (E)/(Z)-cinnamyl-1H-triazoles and regiospecific access to bromomethylcoumarins from Morita–Baylis–Hillman adducts
title_short Azidophosphonium salt-directed chemoselective synthesis of (E)/(Z)-cinnamyl-1H-triazoles and regiospecific access to bromomethylcoumarins from Morita–Baylis–Hillman adducts
title_full Azidophosphonium salt-directed chemoselective synthesis of (E)/(Z)-cinnamyl-1H-triazoles and regiospecific access to bromomethylcoumarins from Morita–Baylis–Hillman adducts
title_fullStr Azidophosphonium salt-directed chemoselective synthesis of (E)/(Z)-cinnamyl-1H-triazoles and regiospecific access to bromomethylcoumarins from Morita–Baylis–Hillman adducts
title_full_unstemmed Azidophosphonium salt-directed chemoselective synthesis of (E)/(Z)-cinnamyl-1H-triazoles and regiospecific access to bromomethylcoumarins from Morita–Baylis–Hillman adducts
title_sort azidophosphonium salt-directed chemoselective synthesis of (e)/(z)-cinnamyl-1h-triazoles and regiospecific access to bromomethylcoumarins from morita–baylis–hillman adducts
publisher Beilstein-Institut
series Beilstein Journal of Organic Chemistry
issn 1860-5397
publishDate 2020-07-01
description The direct transformation of Morita–Baylis–Hillman (MBH) adducts into molecules of interest is a crucial process wherein allylic hydroxy-protected or halogenated MBH adducts are commonly preferred. Herein, we report an azidophosphonium salt (AzPS)-catalysed straight forward protocol for synthesising structurally demanding (E)/(Z)-cinnamyl-1H-1,2,3-triazoles and halomethylcoumarins from MBH adducts. The novel methodology, efficient catalyst, and direct utilization of MBH adducts under mild reaction conditions qualify the reported procedures as powerful synthetic tools.
topic halomethylcoumarin
morita–baylis–hillman adducts
organocatalyst
phosphonium salt
triazolation
url https://doi.org/10.3762/bjoc.16.130
work_keys_str_mv AT soundararajankarthikeyan azidophosphoniumsaltdirectedchemoselectivesynthesisofezcinnamyl1htriazolesandregiospecificaccesstobromomethylcoumarinsfrommoritabaylishillmanadducts
AT radhakrishnanshobana azidophosphoniumsaltdirectedchemoselectivesynthesisofezcinnamyl1htriazolesandregiospecificaccesstobromomethylcoumarinsfrommoritabaylishillmanadducts
AT kamarajapurathurajusubimol azidophosphoniumsaltdirectedchemoselectivesynthesisofezcinnamyl1htriazolesandregiospecificaccesstobromomethylcoumarinsfrommoritabaylishillmanadducts
AT jhelenratnamonica azidophosphoniumsaltdirectedchemoselectivesynthesisofezcinnamyl1htriazolesandregiospecificaccesstobromomethylcoumarinsfrommoritabaylishillmanadducts
AT ayyanothkarthikkrishnakumar azidophosphoniumsaltdirectedchemoselectivesynthesisofezcinnamyl1htriazolesandregiospecificaccesstobromomethylcoumarinsfrommoritabaylishillmanadducts
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