Synthesis of Novel Hexaazaisowurtzitane Cages to Access CL‐20

Kommu, Nagarjuna; Aravindu, Pampuram; Rani, Karike Durga; shaik, Adul Munaf; Rao, Venkat K.

doi:10.1002/ajoc.202100680

Cited by 6 publications

(1 citation statement)

References 42 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Hexaazaisowurtzitane derivatives can only be obtained in acceptable yields by the condensation of glyoxal with benzylamine (its derivatives), benzylamine-like compounds (a series of amines bearing an aromatic moiety linked via a methylene bridge to the amino group), allylamine (or similar compounds) and, as it turned out most recently, with a primary amine where the amino group is linked to the strained aliphatic ring such as cyclopropylamine and cyclobutylamine [15,23,98,99].…”

Section: Introductionmentioning

confidence: 99%

Condensation of Benzyl Carbamate with Glyoxal in Polar Protic and Aprotic Solvents

Paromov

2023

Molecules

View full text Add to dashboard Cite

The synthesis of substituted 2,4,6,8,10,12-hexaazaisowurtzitane via direct condensation is challenging. The selection of starting ammonia derivatives is very limited. The important step in developing alternative synthetic routes to these compounds is to investigate their formation process in detail. Here, we examined an acid-catalyzed condensation between benzyl carbamate and glyoxal in a ratio of 2:1 in a range of polar protic and aprotic solvents, and discovered a new process occurring during the cascade condensation of glyoxal with ammonia derivatives as well as discovered several processes hindering the formation of caged compounds. More specifically, a cyclic compound, N,N′-bis(carbobenzoxy)-3,6-diamino-1,4-dioxane-2,5-diol, was found to form at the early stage of condensation under low acidity conditions. The formation of this compound is governed by an easier condensation of alcohol groups compared to the amide ones. The condensation intermediates, N,N′-bis(carbobenzoxy)ethan-1,2-diol, N,N′,N″-tris(carbobenzoxy)ethanol, and N,N′,N″,N‴-tetrakis(carbobenzoxy)ethan, were obtained at a higher acidity. A range of solvents were identified: those that react with benzyl carbamate, those that promote the progress of side processes, and those that promote precipitation of condensation intermediates. A few byproducts were isolated and identified. It was found that DMSO exhibits a strong deactivating ability, while CH3CN exhibits a strong activating ability towards the acid-catalyzed condensation process of benzyl carbamate with glyoxal.

show abstract

Section: Introductionmentioning

confidence: 99%

Condensation of Benzyl Carbamate with Glyoxal in Polar Protic and Aprotic Solvents

Paromov

2023

Molecules

View full text Add to dashboard Cite

show abstract

Rediscovering N‐Methyltetranitropyrrole – A Versatile High Energy Material via Facile Two‐step Eco‐friendly Synthetic Approach

et al. 2022

View full text Add to dashboard Cite

A highly efficient 2-step method, where three nitro groups could be directly introduced upon pyrrole moiety in a single step, was developed as an environmentally benign process for the synthesis of N-methyltetranitropyrrole (1) employing metal nitrate/conc. sulphuric acid as the nitrating reagent. This method resulted 1 in high purity having higher thermal stability (273 °C) along with reduced sensitivity (impact sensitivity > 40 J; fricition sensitivity > 360 N), which makes it a versatile high energy material. An over-oxidized new product 1-methyl-3,3,4,4-tetranitropyrrolidine-2,5-dione (4) was also isolated during optimization, whose energetic properties are similar to those of RDX.

show abstract

Research progress on design, synthesis and performance of energetic polynitro hexaazaisowurtzitane derivatives: Towards improved CL-20 analogues

Parakhin

Smirnov

2024

FirePhysChem

View full text Add to dashboard Cite

Synthesis of Novel Hexaazaisowurtzitane Cages to Access CL‐20

Cited by 6 publications

References 42 publications

Condensation of Benzyl Carbamate with Glyoxal in Polar Protic and Aprotic Solvents

Condensation of Benzyl Carbamate with Glyoxal in Polar Protic and Aprotic Solvents

Rediscovering N‐Methyltetranitropyrrole – A Versatile High Energy Material via Facile Two‐step Eco‐friendly Synthetic Approach

Research progress on design, synthesis and performance of energetic polynitro hexaazaisowurtzitane derivatives: Towards improved CL-20 analogues

Contact Info

Product

Resources

About