New research progress on 286961-14-6 in 2021. 286961-14-6, Name is tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate, molecular formula is C16H28BNO4, SDS of cas: 286961-14-6, SMILES is O=C(N1CCC(B2OC(C)(C)C(C)(C)O2)=CC1)OC(C)(C)C belongs to naphthyridine compound, is a common compound. In a patnet, author is Sirakanyan, Samvel N., once mentioned the new application about 286961-14-6.
Background and Objective: Continuing our studies in the field of a new rearrangement in the 2,7-naphthyridine series, the synthesis and rearrangement of mono-2 and di-amino derivatives 3 of 2,7-naphthyridine was carried out. Taking into account the wide range of pharmacological activities of pyrazole derivatives the synthesis of some 3-amino-1-(3,5-dimethyl-1H-pyrazol-1-yl)-2,7-naphthyridines 8 and of pyrazolo[3,4-c]-2,7-naphthyridine 12 was described. Methods: Compounds 2 were reacted with amines furnishing the relevant rearrangement products 4. Starting from the 7-benzyl-3-chloro-1-hydrazino-5,6,7,8-tetrahydro-2,7-naphthyridine-4-carbonitrile 6 and 5-hydrazino-6,7,8,9- tetrahydro-3H-pyrazolo[3,4-c]-2,7-naphthyridin-1-amine 12 the 7-benzyl-3-chloro-1-(3,5-dimethyl-1H-pyrazol- 1-yl)-5,6,7,8-tetrahydro-2,7-naphthyridine-4-carbonitrile 7 and 3,5-dimethyl-1H-pyrazol-1-yl-9,11-dimethylpyrimido[1′, 2′: 1,5] pyrazolo[3,4-c]-2,7-naphthyridine 13 were synthesized, via the Knorr synthesis of pyrazoles. Results: The syntheses of 2-benzyl-6,8-diamino-3,4-dihydro-2,7-naphthyridin-1(2H) ones 4 deriving from the rearrangement of compounds 2 and/or 3 were performed. By reaction with benzylamine compound 2a or 3g gave the unexpected formation of N, 7-dibenzyl-8-(benzylimino)-3-pyrrolidin-1-yl-5,6,7,8-tetrahydro-2,7-naphthyridin- 1-amine 5: in fact, the rearrangement was followed by condensation between the C-1 carbonyl group of the 2,7-naphthyridine ring and the benzylamine. Starting from the 7-benzyl-3-chloro-1-(3,5-dimethyl-1H- pyrazol-1-yl)-5,6,7,8-tetrahydro-2,7-naphthyridine-4-carbonitrile 7 the relevant 3-amino-7-benzyl-1-(3,5-dimethyl- 1H-pyrazol-1-yl)-5,6,7,8-tetrahydro-2,7-naphthyridine-4-carbonitriles 8 were obtained. In harsh experimental conditions the nucleophilic substitution of the 1-pyrazolyl residue took place with formation of 7-benzyl- 1,3-bis[(2-hydroxypropyl) amino]-5,6,7,8-tetrahydro-2,7-naphthyridine-4-carbonitrile 10. Moreover, compound 7 reacted with hydrazine hydrate giving the pyrazolo[3,4-c]-2,7-naphthyridine 12, which, in turn, furnished a new tetra-heterocyclic system: 3-benzyl-5-(3,5-dimethyl-1H-pyrazol-1-yl)-9,11-dimethyl-1,2,3,4-tetrahydropyrimido[1′, 2′: 1,5] pyrazolo[3,4-c]-2,7-naphthyridine 13. Conclusion: Replacement of methyl group on piperidine ring of 2,7-naphthyridine system with the benzyl one led to new results. Reaction of compound 2a or 3g with benzylamine brought to an unexpected formation of N, 7-dibenzyl-8-(benzylimino)-3-pyrrolidin-1-yl-5,6,7,8-tetrahydro-2,7-naphthyridin-1-amine 5. The reactivity of 7-benzyl-3-chloro-1-(3,5-dimethyl-1H-pyrazol-1-yl)-2,7-naphthyridine 7 with nucleophiles was investigated, observing the unexpected substitution of the 1-pyrazolyl residue.
These may comprise an expansion of the substrate scope from aromatic and heteroaromatic compounds to other hydrocarbons. If you like, you can also browse other articles about this kind. Thanks for taking the time to read the blog about 286961-14-6, SDS of cas: 286961-14-6.
Reference:
1,8-Naphthyridine – Wikipedia,
,1,8-Naphthyridine | C8H6N2 – PubChem