Pd-catalysed general access to 7-membered N/O-heterocyclic compounds as potential agents against inflammation

B. Thirupataiah; Gangireddy Sujeevan Reddy; Guntipally Mounika; Jetta Sandeep Kumar; Kazi Amirul Hossain; Jayesh Mudgal; Jessy E. Mathew; Gautham G. Shenoy; Marina Rajadurai; Kishore V.L. Parsa; Manojit Pal

doi:10.1039/d1cc04140a

Pd-catalysed general access to 7-membered N/O-heterocyclic compounds as potential agents against inflammation

B. Thirupataiah
, Gangireddy Sujeevan Reddy
, Guntipally Mounika
, Jetta Sandeep Kumar
, Kazi Amirul Hossain
, Jayesh Mudgal
, Jessy E. Mathew
, Gautham G. Shenoy
, Marina Rajadurai
, Kishore V.L. Parsa
, Manojit Pal^*

^*Corresponding author for this work

Department of Pharmacology, Manipal College of Pharmaceutical Sciences, Manipal
Department of Pharmaceutical Chemistry, Manipal College of Pharmaceutical Sciences, Manipal

Research output: Contribution to journal › Article › peer-review

5 Citations (Scopus)

Abstract

A Pd-catalysed regioselective synthesis of 4,5-disubstituted 7-membered N/O-heterocycles was achievedviathe 7-endo-digcyclization followed by C-C bond formation of 2-(1-alkynyl)phenylacetamide. The ligand/additive free cascade reaction proceeded in the presence of PdCl₂in aqueous MeCN when the separate and individual use of methyl vinyl ketone and allyl bromide generally afforded an O- and N-heterocycle, respectively. The pharmacological assay was performed to identify the first example of a 1H-benzo[d]azepin-2(3H)-one based novel inhibitor of PDE4B.

Original language	English
Pages (from-to)	10091-10094
Number of pages	4
Journal	Chemical Communications
Volume	57
Issue number	78
DOIs	https://doi.org/10.1039/d1cc04140a
Publication status	Published - 07-10-2021

All Science Journal Classification (ASJC) codes

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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10.1039/d1cc04140a

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title = "Pd-catalysed general access to 7-membered N/O-heterocyclic compounds as potential agents against inflammation",

abstract = "A Pd-catalysed regioselective synthesis of 4,5-disubstituted 7-membered N/O-heterocycles was achievedviathe 7-endo-digcyclization followed by C-C bond formation of 2-(1-alkynyl)phenylacetamide. The ligand/additive free cascade reaction proceeded in the presence of PdCl2in aqueous MeCN when the separate and individual use of methyl vinyl ketone and allyl bromide generally afforded an O- and N-heterocycle, respectively. The pharmacological assay was performed to identify the first example of a 1H-benzo[d]azepin-2(3H)-one based novel inhibitor of PDE4B.",

author = "B. Thirupataiah and Reddy, \{Gangireddy Sujeevan\} and Guntipally Mounika and Kumar, \{Jetta Sandeep\} and Hossain, \{Kazi Amirul\} and Jayesh Mudgal and Mathew, \{Jessy E.\} and Shenoy, \{Gautham G.\} and Marina Rajadurai and Parsa, \{Kishore V.L.\} and Manojit Pal",

note = "Funding Information: The authors acknowledge the financial support received from DBT, New Delhi, India (Grant No. BT/PR22126/BRB/10/ 1585/2017). Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2021.",

year = "2021",

month = oct,

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doi = "10.1039/d1cc04140a",

language = "English",

volume = "57",

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journal = "Chemical Communications",

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T1 - Pd-catalysed general access to 7-membered N/O-heterocyclic compounds as potential agents against inflammation

AU - Thirupataiah, B.

AU - Reddy, Gangireddy Sujeevan

AU - Mounika, Guntipally

AU - Kumar, Jetta Sandeep

AU - Hossain, Kazi Amirul

AU - Mudgal, Jayesh

AU - Mathew, Jessy E.

AU - Shenoy, Gautham G.

AU - Rajadurai, Marina

AU - Parsa, Kishore V.L.

AU - Pal, Manojit

N1 - Funding Information: The authors acknowledge the financial support received from DBT, New Delhi, India (Grant No. BT/PR22126/BRB/10/ 1585/2017). Publisher Copyright: © The Royal Society of Chemistry 2021.

PY - 2021/10/7

Y1 - 2021/10/7

N2 - A Pd-catalysed regioselective synthesis of 4,5-disubstituted 7-membered N/O-heterocycles was achievedviathe 7-endo-digcyclization followed by C-C bond formation of 2-(1-alkynyl)phenylacetamide. The ligand/additive free cascade reaction proceeded in the presence of PdCl2in aqueous MeCN when the separate and individual use of methyl vinyl ketone and allyl bromide generally afforded an O- and N-heterocycle, respectively. The pharmacological assay was performed to identify the first example of a 1H-benzo[d]azepin-2(3H)-one based novel inhibitor of PDE4B.

AB - A Pd-catalysed regioselective synthesis of 4,5-disubstituted 7-membered N/O-heterocycles was achievedviathe 7-endo-digcyclization followed by C-C bond formation of 2-(1-alkynyl)phenylacetamide. The ligand/additive free cascade reaction proceeded in the presence of PdCl2in aqueous MeCN when the separate and individual use of methyl vinyl ketone and allyl bromide generally afforded an O- and N-heterocycle, respectively. The pharmacological assay was performed to identify the first example of a 1H-benzo[d]azepin-2(3H)-one based novel inhibitor of PDE4B.

UR - https://www.scopus.com/pages/publications/85116220144

UR - https://www.scopus.com/pages/publications/85116220144#tab=citedBy

U2 - 10.1039/d1cc04140a

DO - 10.1039/d1cc04140a

M3 - Article

C2 - 34515287

AN - SCOPUS:85116220144

SN - 1359-7345

VL - 57

SP - 10091

EP - 10094

JO - Chemical Communications

JF - Chemical Communications

IS - 78

ER -

Pd-catalysed general access to 7-membered N/O-heterocyclic compounds as potential agents against inflammation

Abstract

All Science Journal Classification (ASJC) codes

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