NDLI: A New Approach to the Synthesis of Polyfunctionally Substituted 1,8-Naphthyridin-2-one Derivatives from 6-Azidopyridones: A Novel Thermal Decomposition to 6-Aminopyridones

Please wait, while we are loading the content...

A New Approach to the Synthesis of Polyfunctionally Substituted 1,8-Naphthyridin-2-one Derivatives from 6-Azidopyridones: A Novel Thermal Decomposition to 6-Aminopyridones

Content Provider	Scilit
Author	Mekheimer, Ramadan Ahmed
Copyright Year	2001
Description	Azidation of the chloroaldehyde 2, which was obtained from the 6-hydroxy-2-pyridones 1, afforded the 6-azido-2-pyridones 3. Compound 3 can be converted to the corresponding 6-amino-2-pyridones 5, by the reaction with triphenylphosphine via phosphazenes and subsequent hydrolysis (Staudinger reaction). This obtained amine 5 reacts with ethyl cyanoacetate in an ethanolic solution containing piperidine to give 7-amino-6-carbethoxy-3-cyano-1,4-dimethyl-1,8-naphthyridin-2(1H)-one (9). Reaction of 9 with dimethylformamide dimethyl acetal, triethylorthoformate and hydrazine hydrate furnished the new 1,8-naphthyridin-2-ones 10, 11 and 12, respectively, in good yields. On the other hand, refluxing 9 with piperidine or morpholine, as secondary amines, did not afford the corresponding 1,8-naphthyridin-2-ones 13, but instead it undergoes a thermal decomposition under these reaction conditions to yield the unexpected 6-amino-3-cyano-1,4-dimethyl-pyridin-2(1H)-one (14).
Related Links	http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-2001-9749.pdf
Ending Page	0107
Page Count	5
Starting Page	0103
ISSN	00397881
e-ISSN	1437210X
DOI	10.1055/s-2001-9749
Journal	Synthesis
Issue Number	01
Volume Number	2001
Language	English
Publisher	Georg Thieme Verlag KG
Publisher Date	2001-12-31
Access Restriction	Open
Subject Keyword	Journal: Synthesis Organic Chemistry 8-naphthyridin-2-ones Thermal Decomposition 6-amino-3-cyano-1 4-dimethyl-pyridin-2(1h)-one
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

Sl.	Authority	Responsibilities	Communication Details
1	Ministry of Education (GoI), Department of Higher Education	Sanctioning Authority	https://www.education.gov.in/ict-initiatives
2	Indian Institute of Technology Kharagpur	Host Institute of the Project: The host institute of the project is responsible for providing infrastructure support and hosting the project	https://www.iitkgp.ac.in
3	National Digital Library of India Office, Indian Institute of Technology Kharagpur	The administrative and infrastructural headquarters of the project	Dr. B. Sutradhar bsutra@ndl.gov.in
4	Project PI / Joint PI	Principal Investigator and Joint Principal Investigators of the project	Dr. B. Sutradhar bsutra@ndl.gov.in Prof. Saswat Chakrabarti will be added soon
5	Website/Portal (Helpdesk)	Queries regarding NDLI and its services	support@ndl.gov.in
6	Contents and Copyright Issues	Queries related to content curation and copyright issues	content@ndl.gov.in
7	National Digital Library of India Club (NDLI Club)	Queries related to NDLI Club formation, support, user awareness program, seminar/symposium, collaboration, social media, promotion, and outreach	clubsupport@ndl.gov.in
8	Digital Preservation Centre (DPC)	Assistance with digitizing and archiving copyright-free printed books	dpc@ndl.gov.in
9	IDR Setup or Support	Queries related to establishment and support of Institutional Digital Repository (IDR) and IDR workshops	idr@ndl.gov.in

1,8-Naphthyridines II: synthesis of novel polyfunctionally substituted 1,8-naphthyridinones and their degradation to 6-aminopyridones

1,8-Naphthyridines II: synthesis of novel polyfunctionally substituted 1,8-naphthyridinones and their degradation to 6-aminopyridones

Synthesis of 6-Bromomethyl-substituted Derivatives of Pyridin-2(1H)-ones and Their Reaction with Nucleophiles

One-pot synthesis of new series of pyranopyridine derivatives using 3-cyano-6-hydroxy-4-methyl-pyridin-2(1H)-one as a novel nucleophile

Synthesis of 3-Hydroxy-2-Phenyl-1,8-Naphthyridin-4(1H)-one derivatives

Synthesis of naphthyridin-2(1H)-one derivatives via ring expansion of 3-substituted-1H-pyrrolo[2,3-b]pyridin-2(3H)-one derivatives.

Synthesis of 3-S-hetaryl-substituted pyridin-2(1H)-ones and 5,6-dihydropyridin-2(1H)-ones*

Synthesis of 1‐Amino‐5,6‐diaryl‐3‐cyano‐1H‐pyridin‐2‐ones and 6,7‐Diaryl‐4‐cyano‐3‐hydroxy‐1H‐[1,2]diazepines from Isoflavones

A Facile Synthesis of Substituted 6-Amino-2-methylthio-4H-thiopyran-4-ones

A New Approach to the Synthesis of Polyfunctionally Substituted 1,8-Naphthyridin-2-one Derivatives from 6-Azidopyridones: A Novel Thermal Decomposition to 6-Aminopyridones

Similar Documents

1,8-Naphthyridines II: synthesis of novel polyfunctionally substituted 1,8-naphthyridinones and their degradation to 6-aminopyridones

1,8-Naphthyridines II: synthesis of novel polyfunctionally substituted 1,8-naphthyridinones and their degradation to 6-aminopyridones

Synthesis of 6-Bromomethyl-substituted Derivatives of Pyridin-2(1H)-ones and Their Reaction with Nucleophiles

One-pot synthesis of new series of pyranopyridine derivatives using 3-cyano-6-hydroxy-4-methyl-pyridin-2(1H)-one as a novel nucleophile

Synthesis of 3-Hydroxy-2-Phenyl-1,8-Naphthyridin-4(1H)-one derivatives

Synthesis of naphthyridin-2(1H)-one derivatives via ring expansion of 3-substituted-1H-pyrrolo[2,3-b]pyridin-2(3H)-one derivatives.

Synthesis of 3-S-hetaryl-substituted pyridin-2(1H)-ones and 5,6-dihydropyridin-2(1H)-ones*

Synthesis of 1‐Amino‐5,6‐diaryl‐3‐cyano‐1H‐pyridin‐2‐ones and 6,7‐Diaryl‐4‐cyano‐3‐hydroxy‐1H‐[1,2]diazepines from Isoflavones

A Facile Synthesis of Substituted 6-Amino-2-methylthio-4H-thiopyran-4-ones

A New Approach to the Synthesis of Polyfunctionally Substituted 1,8-Naphthyridin-2-one Derivatives from 6-Azidopyridones: A Novel Thermal Decomposition to 6-Aminopyridones