Synthesis of Tetrazines from N-Allenylpyrrole-2-carbaldehydes and pH-Controlled Reversible Fragmentation
Svetlana V Martynovskaya1, Elena A Gyrgenova1, Igor A Ushakov1
1Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St, 664033 Irkutsk, Russian Federation.
Abstract:
A one-pot highly selective approach to the synthesis of hitherto unknown tetrahydropyrrolo[2',1':3,4]pyrazino[1,2-b]pyrrolo[2',1':3,4]pyrazino[1,2-e][1,2,4,5]tetrazine ensembles from simple and available N-allenylpyrrole-2-carbaldehydes and hydrazines has been developed. The reaction proceeds in a very facile manner and tolerates different substituents in both pyrroles and hydrazines. The novel class of organic compounds, tetrahydrodipyrrolodipyrazinotetrazines, proves to be promising pH-sensitive switchers to deliver N-aminopyrrolopyrazinium salts in acidic media and then again tetrahydrodipyrrolodipyrazinotetrazines in basic media. Both transformations give the products in quantitative yields.
More Related Videos
Related Concept Videos
Nucleophilic Aromatic Substitution: Elimination–Addition
Preparation of 1° Amines: Gabriel Synthesis
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
Mass Spectrometry: Alkyne Fragmentation
Preparation of Alkynes: Alkylation Reaction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.


