Cyclization of Methyl-Coumalate-Derived Methyl 1-Benzamido-6-oxo-1,6-dihydropyridine-3-carboxylates: Assembly of the [1,2,4]Triazolo[1,5-a]pyridine Ring System

2017 ◽  
Vol 82 (12) ◽  
pp. 6279-6288 ◽  
Author(s):  
Harold Moloney ◽  
Nicholas A. Magnus ◽  
Jonas Y. Buser ◽  
Matthew C. Embry
Keyword(s):  
2000 ◽  
Vol 41 (52) ◽  
pp. 10251-10255 ◽  
Author(s):  
Masashi Ohba ◽  
Rie Izuta ◽  
Emi Shimizu
Keyword(s):  

ChemInform ◽  
2010 ◽  
Vol 32 (36) ◽  
pp. no-no
Author(s):  
Lalgudi S. Harikrishnan ◽  
Terri L. Boehm ◽  
H. D. Hollis Showalter

2018 ◽  
Vol 54 (100) ◽  
pp. 14128-14131 ◽  
Author(s):  
Tao Jin ◽  
Hongdong Yuan ◽  
Shikuan Su ◽  
Xueshun Jia ◽  
Chunju Li ◽  
...  

A DABCO-catalyzed annulation reaction of pyridin-2-amine and substituted allenoates enables the ring-opening of a pyridine ring system and the formation of two new rings including a pyrimidinone ring and a benzene ring.


1992 ◽  
Vol 70 (5) ◽  
pp. 1288-1295 ◽  
Author(s):  
John E. Francis ◽  
Michael A. Moskal

A short general synthesis of 5-substituted 5,7-diaminoimidazo[4,5-b]pyridines from 5-amino-4-imidazolecarboxamide riboside (AICA riboside) was designed to prepare isosteres of substituted 2-aminoadenosines that are selective adenosine A2 receptor agonists. AICA riboside was converted to a hydroxyl-protected 5-amino-4-imidazolecarbonitrile riboside and reacted with an N,N-disubstituted acetamide in the presence of phosphoryl chloride. Sodium hydride treatment completed the ring closure and introduced the 7-amino group. The hydroxyl protecting groups were removed under standard conditions. N-Substitution of the acetamide by one benzyl moiety led to a 5-N-substituted derivative through hydrogenolysis whereas N,N-dibenzylacetamide led to the 5,7-diamino compound. A 6-methyl analog was obtained from an N,N-disubstituted propionamide. This synthesis may be adapted to other heterocyclic systems, as illustrated by the preparation of an example of the imidazo[4,5-b]pyrrolo[3,2-e]pyridine ring system.


1995 ◽  
Vol 126 (11) ◽  
pp. 1213-1215 ◽  
Author(s):  
G. Haj�s ◽  
G. Tim�ri ◽  
A. Messmer ◽  
A. Zagyva ◽  
I. Miskolczi ◽  
...  

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