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An efficient method was developed for the synthesis of 5,7-dinitroquinoline and its N-oxide. The reactions of these compounds with either thiols or sodium azide resulted in the regiospecific substitution of 5-NO 2 group and the formation of previously unknown quinoline derivatives.The 5-azido derivatives underwentr eactions with 1,3-dicarbonyl compounds and, depending on the nature of reagent, afforded either 5-(1,2,3-triazol)-1-yl-or 5-amino-7-nitroquinolines, which have been previously inaccessible by using other methods.Scheme1.Synthesis of 5,7-dinitroquinolines 1 and 2 (DMF = N,N-dimethylformamide). [a] Dr.A .M.S tarosotnikov,V .V .Nikol'skiy,A.N.B orodulya, Dr.Scheme2.Reactions of 5,7-dinitroquinolines with O-and N-nucleophiles. Scheme3.Reactions of 5,7-dinitroquinolines with thiols. Scheme4.Nucleophilic aromatic substitution of the nitro group(Nu = nuclophile).

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“…This step is then followed by the elimination of the NO 2 − group . It is known (see for example ref …”

Section: Resultsmentioning

confidence: 99%

Synthesis and Functionalization of 5,7‐Dinitroquinoline and Its N‐Oxide

et al. 2016

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“…These data are similar to those obtained for 7 polyfluoroalkoxy 1,5 dinitro 3 azabicyclo[3.3.1]non 6 enes. 12, 13 In the reaction of 3 cyano 4,6 dinitro 1 (4 nitro phenyl)indazole 7, which was prepared by the nitration of the corresponding N phenyl derivative, 14 with NaBH 4 , the reduction is selective (only at the dinitrophenyl frag ment), and the subsequent double Mannich reaction with formaldehyde and glycine affords tricyclic derivative 8 in good yield (Scheme 3).…”

Section: Methodsmentioning

confidence: 99%

“…MeI, NaOH, MeCN, 20 °C; ii. MeI, K 2 CO 3 , DMF, 20 °C The structure of the previously unknown compound 16 was determined by 1 H, 13 C, 14 To sum up, we developed a general method for the synthesis of 3 R 1,5 dinitro 3 azabicyclo[3.3.1]nonanes fused with azole (pyrazole, thiazole, and triazole) rings based on a series of meta dinitro substituted benzazoles.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of 3-R-1,5-dinitro-3-azabicyclo[3.3.1]nonanes fused to azoles

et al. 2009

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“…When hydrazones 73 are treated with alkali or alkaline metal carbonates, 1-aryl-4,6-dinitro-3-formyl-1Н-indazoles 74 are formed due to intramolecular substitution of the nitro group. 73,74 When 74 is treated with hydrochloric hydroxylamine in formic acid, nitrile 74а is obtained.…”

Section: Synthesis Of Benzannelated Five-membered Heterocycles With Tmentioning

confidence: 99%

Synthesis of benzannelated five-membered heteroaromatic compounds from 2,4,6-trinitrotoluene

Bastrakov¹,

Старосотников²,

Шевелев

2008

Arkivoc

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Methods for the synthesis of five-membered benzannelated heterocyclic compounds from the military explosive 2,4,6-trinitrotoluene (TNT) are summarised. The general approach concerns the transformation of the TNT methyl group followed by either intramolecular substitution of the ortho-nitro group or regioselective substitution of the ortho-nitro group by an appropriate nucleophile and subsequent cyclization.

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Cited by 20 publications

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Synthesis and Functionalization of 5,7‐Dinitroquinoline and Its N‐Oxide

Synthesis and Functionalization of 5,7‐Dinitroquinoline and Its N‐Oxide

Synthesis of 3-R-1,5-dinitro-3-azabicyclo[3.3.1]nonanes fused to azoles

Synthesis of benzannelated five-membered heteroaromatic compounds from 2,4,6-trinitrotoluene

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