Synthesis of novel 2‐aminoimidazo[4,5‐<i>b</i>]pyridines, including the thieno analogue of the cooked‐food mutagen IFP

Björk, Malin; Grivas, Spiros

doi:10.1002/jhet.5570430116

Cited by 17 publications

(11 citation statements)

References 83 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…In particular, thieno In an analogous reaction, fused heterocyclic compounds 126 were obtained in 45-98% yields from o-aminothiophenecarbaldehydes 127a-c and creatinine in the presence of bis(trimethylsilyl)acetamide (Scheme 72). 93…”

Section: Quinolines and Heterofused Pyridinesmentioning

confidence: 99%

Organosilicon Compounds as Water Scavengers in Reactions of Carbonyl Compounds

Volochnyuk¹,

Plaskon²,

Grygorenko³

2009

Synthesis

View full text Add to dashboard Cite

show abstract

Section: Quinolines and Heterofused Pyridinesmentioning

confidence: 99%

Organosilicon Compounds as Water Scavengers in Reactions of Carbonyl Compounds

Volochnyuk¹,

Plaskon²,

Grygorenko³

2009

Synthesis

View full text Add to dashboard Cite

show abstract

“…Thus, aldehyde 101 quantitatively reacts with creatinine to form compound 102. 177 Creatinine was activated by converting to the corresponding O-silylenolate using bis(trimethylsilyl)acetamide, which also turned out to be a suitable solvent (Scheme 41).…”

Section: Construction Of Thienopyridine System Through the Formation mentioning

confidence: 99%

Recent advances in the chemistry of thieno[2,3-b]pyridines 1. Methods of synthesis of thieno[2,3-b]pyridines

et al. 2020

View full text Add to dashboard Cite

show abstract

“…It is known [2][3][4] that the thiophene ring in a thienopyridine fragment can readily undergo desulfurization with opening of the thiophene ring. In this work we report results of a study of the condensed pyrrolodiazepines transformation which contain a thieno [2,3-b]pyridine fragment.…”

mentioning

confidence: 99%

Desulfurization of pyrido[3′,2′:4,5]thieno-[2,3-f]pyrrolo[1,2-a][1,4]diazepines

Red'kin

Строганова

Vasilin

et al. 2012

Chem Heterocycl Comp

View full text Add to dashboard Cite

Pyrrolo[1,2-a] [1,4]diazepine derivatives are of interest from the viewpoint of searching for and developing novel substances with a variety of types of biological activity. For many years this fact has stimulated an active search for methods of synthesizing and modifying compounds of this class [1].It is known [2-4] that the thiophene ring in a thienopyridine fragment can readily undergo desulfurization with opening of the thiophene ring. In this work we report results of a study of the condensed pyrrolodiazepines transformation which contain a thieno[2,3-b]pyridine fragment.Amongst these derivatives we have examined the tetracyclic system of pyridothienopyrrolodiazepines 1a,b prepared by recyclization of N-(5-methylfuran-2-yl)methyl-substituted derivatives of 3-aminothieno[2,3-b]-pyridine amides using a known method [5] and we have looked at their reactions in the presence of Raney nickel.It was found that refluxing the diazepines 1a,b in ethanol in the presence of activated Raney nickel gave the desulfurization products, pyrrolodiazepines 2a,b which contain a pyridine ring conjugated to the diazepine fragment and whose structures were proved using NMR and mass spectrometric methods N S Me R Me NH 2 O N H O Me HCl / AcOH N S Me R Me NH N O Me N Me R Me NH N O Me EtOH 1a,b 60 o C 2a,bRaney Ni, 1,2a R = H, b R = Br 1 H and 13 C NMR spectra were recorded on a Bruker AM-300 instrument (300 and 75 MHz respectively) using DMSO-d 6 with TMS as internal standard. Mass spectra were taken on a Kratos MS-30 spectrometer with direct introduction of the sample into the ion source (EI, 70 eV).Compounds 1a,b were prepared by the method reported in [4]. Melting points and spectroscopic data agreed with those in the literature.

show abstract

Synthesis of novel 2‐aminoimidazo[4,5‐b]pyridines, including the thieno analogue of the cooked‐food mutagen IFP

Cited by 17 publications

References 83 publications

Organosilicon Compounds as Water Scavengers in Reactions of Carbonyl Compounds

Organosilicon Compounds as Water Scavengers in Reactions of Carbonyl Compounds

Recent advances in the chemistry of thieno[2,3-b]pyridines 1. Methods of synthesis of thieno[2,3-b]pyridines

Desulfurization of pyrido[3′,2′:4,5]thieno-[2,3-f]pyrrolo[1,2-a][1,4]diazepines

Contact Info

Product

Resources

About