US EPA

7426559 

Journal Article 

Microwave-assisted synthesis of novel (5-nitropyridin-2-yl)alkyl and (5-nitropyridin-3-yl)alkyl carbamates 

Henry, C; Haupt, A; Turner, SC; , 

2009 

Yes 

Journal of Organic Chemistry
ISSN: 0022-3263
EISSN: 1520-6904 

AMER CHEMICAL SOC 

WASHINGTON 

74 

5 

1932-1938 

English 

19175330 

10.1021/jo802439d 

WOS:000263921700014 

https://pubs.acs.org/doi/10.1021/jo802439d
Exit
 

A straightforward approach to novel (5-nitropyridin-2-yl)alkyl and (5-nitropyridin-3-yl)alkyl carbamate building blocks is presented in this study. Their construction is achieved by condensation of N-carbamate alpha- and beta-amino carbonyl derivatives with 1-methyl-3,5-dinitro-2-pyridone 1 under microwave irradiation. Judiciously chosen modifications in the nature of the parent carbonyl starting material has influenced the regiochemical outcome of the reaction and allowed an efficient access to novel nitrogen-containing scaffolds. Compounds sharing morphological similarities have been gathered in three libraries differing from each other in a single structural parameter. 

2-pyridone; [carbonyl; Building blocks; Carbonyl derivatives; Microwave-assisted synthesis; Regiochemical; Starting materials; Structural parameters; Amines; Carbonylation; Chemical modification; Microwave irradiation; Organic compounds; Alkylation; 1 methyl 3,5 dinitro 2 pyridone; benzyl 3,4 dihydro 7 nitro 2h pyrano[3,2 b]pyridin 3 ylcarbamate; benzyl 5,6,7,8 tetrahydro 3 nitroquinolin 7 ylcarbamate; benzyl 6,8 dihydro 3 nitro 5h pyrano[3,4 b]pyridin 5 ylcarbamate; benzyl(5 nitropyridin 3 yl)methylcarbamate; carbamic acid derivative; carbonyl derivative; nitrogen; pyridone derivative; tert butyl 2 (5 nitropyridin 2 yl)cyclopentylcarbamate; tert butyl 2 (5 nitropyridin 2 yl)pyrrolidine 1 carboxylate; tert butyl 2 (5 nitropyridin 2 yl)thiazolidine 3 carboxylate; tert butyl 2 (5 nitropyridin 3 yl)pyrrolidine 1 carboxylate; tert butyl 3 nitro 5h pyrrolo[3,4 b]pyridine 6 (7h)carboxylate; tert butyl 5,6 dihydro 3 nitro 1,7 naphthyridine 7(8h)carboxylate; unclassified drug; article; drug synthesis; microwave irradiation; polymerization; Carbamates; Cyclization; Microwaves; Molecular Structure; Pyridines; Stereoisomerism