Transformation of 4-Substituted Tetrahydro-Pyrrolobenzodiazepines in a Three-Component Reaction With Methyl Propiolate and Indole

Voskressensky, Leonid G.; Борисова, Т. Н.; Babakhanova, M. I.; Титов, А. А.; Chervyakova, T. M.; Новиков, Роман А.; Бутин, А. В.; Khrustalev, Victor N.; Varlamov, A. V.

doi:10.1007/s10593-014-1431-5

Cited by 7 publications

(3 citation statements)

References 5 publications

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“…Previously, the pyrrolo[1,2-a][1,4]benzodiazepine (PBD) scaffold was prepared via Pictet-Spengler [30,31] reaction with further oxidation with MnO 2 (Scheme 1, path A) or Bischler-Napieralski [30,32] reaction (Scheme 1, path B).…”

Section: Resultsmentioning

confidence: 99%

Synthesis Of Dipyrrolobenzo[1,2‐a : 2′,1′‐c][1,4]diazepine Scaffold Via Three‐Component Reaction

Zinoveva,

Borisova,

Podchufarova

et al. 2024

Asian J Org Chem

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A three component reaction employing readily available starting materials: 2‐(1‐pyrrolyl)benzylamine, arylglyoxal monohydrates and electron‐deficient alkenes in the synthesis of dipyrrolobenzo[1,2‐a:2',1'‐c][1,4]diazepines ‐ previously undescribed system and indolo[2,1‐c]pyrrolo[1,2‐a][1,4]benzodiazepine derivatives have been shown. Domino reactions of pyrrolo[1,2‐a][1,4]benzodiazepines with electron‐deficient alkenes has been proposed as another approach. The applicability of the three‐component reaction for the synthesis of indolizino[8,7‐b]indole derivatives from tryptamine has been studied. The in vitro biological activity of title compounds has been tested.

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Section: Resultsmentioning

confidence: 99%

Synthesis Of Dipyrrolobenzo[1,2‐a : 2′,1′‐c][1,4]diazepine Scaffold Via Three‐Component Reaction

Zinoveva,

Borisova,

Podchufarova

et al. 2024

Asian J Org Chem

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“…The parent PBD 6a required heating the amine with ethyl formate to give formamide 234c and then cyclisation with phosphoryl chloride at 40 °C while PBD 6c was prepared by coupling the amine with protected glycine 235 in the presence of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDAC.HCl) to produce amide 234c and then cyclisation using similar reaction conditions. In two recent publications Voskressensky et al [85,86] used the same methodology to synthesise novel PBDs 6b , d – g from amine 218a via cyclisation of amides 234b , d – g . The yields of the Bischler–Napieralski cyclisation step are noted to be from 74% with up to quantitative yield.…”

Section: Synthesis Of Pyrrolo[14]benzodiazepinesmentioning

confidence: 99%

An Update on the Synthesis of Pyrrolo[1,4]benzodiazepines

Varvounis

2016

Molecules

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Pyrrolo [1,4]benzodiazepines are tricyclic compounds that are considered "privileged structures" since they possess a wide range of biological activities. The first encounter with these molecules was the isolation of anthramycin from cultures of Streptomyces, followed by determination of the X-ray crystal structure of the molecule and a study of its interaction with DNA. This opened up an intensive synthetic and biological study of the pyrrolo

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“…[9] A literature survey showed that the direction of the ring-expansion reaction was depended on many effects including substrates, substituents and reaction conditions. [10] Although there have been a couple of reports about this kind of ring-expansion reactions, this ring-expansion reaction still suffered from some drawbacks such as multiple reaction pathways, instability and lower yields. Therefore, developing efficient synthetic protocols for various N-containing heterocycles based on this kind of ring-expansion reaction is welcomed for the organic synthesis and medicinal chemistry.…”

Section: Introductionmentioning

confidence: 99%

One‐Pot Sequential [3+2] Cycloaddition and Ring‐Expansion Reaction for Selective Synthesis of Polycyclic Spirooxindole

Han

et al. 2022

ChemistrySelect

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The one-pot three-component reaction of L-proline, isatins and 1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-ones and sequential reaction with methyl propiolate in refluxing methanol resulted in novel functionalized spiro[chromane-2,3'-indoline]-2',4-diones as major products and spiro[chromeno[3,2-d]azocine-2,3'indolin]-3-yl)acrylate as minor products. On the other hand, the similar one-pot-three-component reaction of L-proline, isatins and 3-(2-hydroxyphenyl)-1-phenylprop-2-en-1-ones and sequential reaction with methyl propiolate in refluxing acetonitrile predominately afforded the unique 6b,14-(epoxy[1,2]benzeno)pyrrolo[1',2':1,2]azocino[4,5-c]quinoline-8carboxylates in satisfactory yields.

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Transformation of 4-Substituted Tetrahydro-Pyrrolobenzodiazepines in a Three-Component Reaction With Methyl Propiolate and Indole

Cited by 7 publications

References 5 publications

Synthesis Of Dipyrrolobenzo[1,2‐a : 2′,1′‐c][1,4]diazepine Scaffold Via Three‐Component Reaction

Synthesis Of Dipyrrolobenzo[1,2‐a : 2′,1′‐c][1,4]diazepine Scaffold Via Three‐Component Reaction

An Update on the Synthesis of Pyrrolo[1,4]benzodiazepines

One‐Pot Sequential [3+2] Cycloaddition and Ring‐Expansion Reaction for Selective Synthesis of Polycyclic Spirooxindole

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