Synthesis of substituted 2-alkyl(aryl)thio-3-cyanopyridines and 3-aminothieno[2,3-b]pyridines

Kaigorodova, E. I.; Konyushkin, L. D.; Mikhailichenko, S. N.; Vasilin, V. K.; Kul'nevich, V. G.

doi:10.1007/bf01169240

Cited by 5 publications

(7 citation statements)

References 2 publications

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“…The high stereoselectivity of the Staudinger cycloaddition can be explained by using the current mechanistic model for the ketene‐imine cycloaddition reaction . In accordance with theoretical and experimental studies, interaction of ketenes and imines is a stepwise process, which proceeds via zwitterionic intermediate formation followed by intermolecular conrotatory ring closure to yield four‐membered β‐lactams .…”

Section: Resultsmentioning

confidence: 53%

“…As initial compounds, we have chosen 3‐chloroacetylamino‐2‐aroylthieno[2,3‐ b ]pyridines 1a–c , which were first synthesized from corresponding aminoketones by an acylation according to the earlier described procedure (Scheme ). The acylated aminoketones 1 were converted to 1,4‐diazepines 2 by successive treatment with gaseous NH 3 in anhydrous DMF under heating (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

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Synthesis of β‐Lactam‐containing Pyrido[3′,2′:4,5]thieno[3,2‐e][1,4]diazepines

Строганова

Vasilin

Kovalenko

et al. 2017

Journal of Heterocyclic Chem

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Novel tricyclic 1,4‐diazepine derivatives – pyrido[3′,2′:4,5]thieno[3,2‐e][1,4]diazepin‐2‐ones – have been synthesized. Azetidin‐2‐one moiety has been incorporated into the 1,4‐diazepine scaffold by [2 + 2]cycloaddition of functionalized ketenes to imine C═N bond, and several tetracyclic azetodiazepines which can be considered as potential compounds of biological interest have been prepared. Stereoselectivity of the cycloaddition was proved by NMR and X‐ray analysis data.

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Section: Resultsmentioning

confidence: 53%

Section: Resultsmentioning

confidence: 99%

Synthesis of β‐Lactam‐containing Pyrido[3′,2′:4,5]thieno[3,2‐e][1,4]diazepines

Строганова

Vasilin

Kovalenko

et al. 2017

Journal of Heterocyclic Chem

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“…To further develop our studies on the alkylation of 6-methyl-4-methoxymethyl-3-cyano-2(1H)-pyridinethione (1a) and its structural isomer 1b [4][5][6], the pyridinethiones 1a,b were reacted with 5-nitro-furylmethyl-and 4-nitrobenzyl bromides and the 5-chloromethyl derivative of methyl 2 furoate (Scheme 1). …”

Section: Resultsmentioning

confidence: 99%

“…Experimental General 1H-NMR spectra were recorded on Bruker WM-250 and Tesla BS-487A spectrometers using DMSO-d 6 or CDCl 3 as solvents. Chemical shifts (δ) are given in ppm relative to TMS.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Reactions of Substituted 3-amino-2-furyl(aryl)-thieno[2,3-b]pyridines

et al. 2000

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“…3 We also used N2-substituted N2- (5-methyl-2-furylmethyl)-3-aminothieno[2,3-b]pyridine-2-carboxamides 6, which were synthesized from pyridinethiones 4 and the corresponding furfurylchloroacetamides 5 under Thorpe-Ziegler conditions (Scheme 3). 3,10 We found that the treatment of the amides 3a-d and 6a-f, bearing a tert-butyl or phenyl group as a substituent at the amide function, with concentrated HCl in acetic acid (Method A), did not furnish the expected N-substituted pyrrolodiazepines. Instead, the only products obtained 2008, No.…”

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confidence: 94%

Some Transformations of TertiaryN-Furfurylamides of Aromatic and Heteroaromatic Carboxylic Acids under Acidic Conditions

Строганова¹,

Vasilin²,

Zelenskaya³

et al. 2008

Synthesis

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A c i d -C a t a l y z e d T r a n s f o r m a t i o n s o f t e r t -N -F u r f u r y l c a r b o x a m i d e sAbstract: Acid-catalyzed transformations of tertiary N-furfurylamides of ortho-amino substituted aromatic and heteroaromatic carboxylic acids accompanied by elimination of the furfuryl moiety are investigated.Furan derivatives have been widely applied as useful building blocks in carbo-and heterocyclic compound chemistry for many years and there are numerous reviews devoted to their synthetic application. 1 We have studied the usage of furan compounds for annelated heterocyclic systems synthesis. 2In a preceding paper 3 we presented a new method for the synthesis of pyrrolo[1,2-a]diazepinone derivatives, based on acid-catalyzed transformations of N-One of the advantageous features of our method is the simultaneous formation both of diazepine and pyrrole rings as a result of a furan ring recyclization (Scheme 1).Some pyrrolo[1,2-a][1,4]diazepine derivatives show a wide range of biological activity, including anxiolytic, 4 sedative and antiepileptic activities; 5 they also affect the central nervous system. 6 A number of pyrrolo[1,2-a] [1,4]diazepinone derivatives possess analgesic action, 7 and act as antibacterial 8 and anti-fungal agents with high specificity towards dermatophytes. 9Since diazepine derivatives are of interest in the search for new biologically active compounds and precursors for the manufacture of new medicines, an extension of the developed approach towards the preparation of new pyrrolodiazepines became our main aim.Herein we report our results on acid-catalyzed transformations of tertiary N-furfuryl-containing amino amides of aromatic and heteroaromatic carboxylic acids with an amino function in the ortho position to a carboxy group.As starting compounds we used tertiary amides of orthoaminobenzoic acids 3, which were prepared from secondary furfurylamines 1 according to Scheme 2. 3 We also used N2-substituted N2-(5-methyl-2-furylmethyl)-3-aminothieno[2,3-b]pyridine-2-carboxamides 6, which were synthesized from pyridinethiones 4 and the corresponding furfurylchloroacetamides 5 under Thorpe-Ziegler conditions (Scheme 3). 3,10

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Synthesis of substituted 2-alkyl(aryl)thio-3-cyanopyridines and 3-aminothieno[2,3-b]pyridines

Cited by 5 publications

References 2 publications

Synthesis of β‐Lactam‐containing Pyrido[3′,2′:4,5]thieno[3,2‐e][1,4]diazepines

Synthesis of β‐Lactam‐containing Pyrido[3′,2′:4,5]thieno[3,2‐e][1,4]diazepines

Synthesis and Reactions of Substituted 3-amino-2-furyl(aryl)-thieno[2,3-b]pyridines

Some Transformations of TertiaryN-Furfurylamides of Aromatic and Heteroaromatic Carboxylic Acids under Acidic Conditions

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