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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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",

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doi = "10.1039/d1cc04140a",

language = "English",

volume = "57",

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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

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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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