Reaction of 2,3-dibromo-3-nitroacrylates with N-amino-N″-nitroguanidine

Berestovitskaya, V. M.; Ozerova, O. Yu.; Efimova, T. P.; Novikova, T. A.

doi:10.1134/s1070428015120258

Cited by 4 publications

(2 citation statements)

References 5 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“… [83,84] The versatility of this protocol allowed the synthesis of a library of dehydroamino acid derivatives bearing a halogen and electron‐withdrawing group in α‐position. Reactions of dibromonitroacrylates 82 with o ‐phenylenediamine as well as guanidine [85] and hydrazine derivatives [86] occurred by the similar pathway. These results clearly indicate that the nitro group is much more strong acceptor than alkoxycarbonyl one.…”

Section: Aza‐michael Reaction With Pull‐pull Enoatesmentioning

confidence: 86%

Pull‐Pull Alkenes in the Aza‐Michael Reaction

Rulev

Tyumentsev

2022

Adv Synth Catal

View full text Add to dashboard Cite

Aza‐Michael addition is known to be one of the most exploited reactions in organic chemistry. Taking into account the fact that each seventh reaction in pharmaceutical industry involves the formation of at least one C−N bond, it is not surprising that this reaction is especially valuable for the synthesis of bioactive compounds and drugs. Traditionally, only push‐pull alkenes are regarded as starting material for this reaction. The participation of pull‐pull alkenes as Michael acceptors is much less studied. The presence of two vicinal electron‐withdrawing groups makes them highly reactive in nucleophilic reactions especially with nitrogen‐centered nucleophiles. This feature allows them to be excellent building blocks in the synthesis of bioactive molecules and polyfunctional materials. The review considers the most important and sometimes unexpected results obtained over the last two decades on the conjugate addition of nitrogen nucleophiles to pull‐pull alkenes bearing various acceptor moieties (alkoxycarbonyl‐, carbonyl‐, formyl‐, cyano‐, trifluoromethyl‐ or nitro group) in various combinations.

show abstract

Section: Aza‐michael Reaction With Pull‐pull Enoatesmentioning

confidence: 86%

Pull‐Pull Alkenes in the Aza‐Michael Reaction

Rulev

Tyumentsev

2022

Adv Synth Catal

View full text Add to dashboard Cite

show abstract

“…1-Amino-2-nitroguanidine (ANQ, 1 ) was first synthesized by Phillips in 1928 [1] and has played an important role in the synthesis of valuable biologically active compounds, such as pesticides and medicines [2,3,4,5,6,7,8,9,10,11,12,13,14,15,16]. In recent years, Klapötke has done a lot of research on the application of ANQ in high-energy nitrogen-rich materials, which began to attract significant interest in the field of energetic materials [17,18].…”

Section: Introductionmentioning

confidence: 99%

A Review on the Reactivity of 1-Amino-2-Nitroguanidine (ANQ)

Wang

Cai

Zhao³

et al. 2019

Molecules

View full text Add to dashboard Cite

1-Amino-2-nitroguanidine (ANQ) is a high-energy nitrogen-rich compound with good detonation properties and low sensitivities. ANQ has only a central carbon atom with three small groups around it, including an amino, a hydrazine and a nitroxyl group. Though the molecular structure of ANQ is very simple, its reactivity is surprisingly abundant. ANQ can undergo various reactions, including reduction reaction, acylation reaction, salification reaction, coordination reaction, aldimine condensation reaction, cyclization reaction and azide reaction. Many new energetic compounds were purposely obtained through these reactions. These reactions were systematically summarized in this review, and detonation properties of some energetic compounds were compared. In the field of energetic materials, ANQ and some derivatives exhibit good application prospects.

show abstract