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Reliable Functionalization of 5,6-Fused Bicyclic N-Heterocycles Pyrazolopyrimidines and Imidazopyridazines via Zinc and Magnesium Organometallics.

ABSTRACT: DFT-calculations allow prediction of the reactivity of uncommon N-heterocyclic scaffolds of pyrazolo[1,5-a]pyrimidines and imidazo[1,2-b]pyridazines and considerably facilitate their functionalization. The derivatization of these N-heterocycles was realized using Grignard reagents for nucleophilic additions to 5-chloropyrazolo[1,5-a]pyrimidines and TMP2 Zn ⋅ 2 MgCl2  ⋅ 2 LiCl allowed regioselective zincations. In the case of 6-chloroimidazo[1,2-b]pyridazine, bases such as TMP2 Zn ⋅ MgCl2  ⋅ 2 LiCl, in the presence or absence of BF3  ⋅ OEt2 , led to regioselective metalations at positions 3 or 8. Subsequent functionalizations were achieved with TMPMgCl ⋅ LiCl, producing various polysubstituted derivatives (up to penta-substitution). X-ray analysis confirmed the regioselectivity for key functional heterocycles.

SUBMITTER: Kumar Rout S 

PROVIDER: S-EPMC9321601 | biostudies-literature | 2022 Jun

REPOSITORIES: biostudies-literature

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Reliable Functionalization of 5,6-Fused Bicyclic N-Heterocycles Pyrazolopyrimidines and Imidazopyridazines via Zinc and Magnesium Organometallics.

Kumar Rout Saroj S   Kastrati Agonist A   Jangra Harish H   Schwärzer Kuno K   Sunagatullina Alisa S AS   Garny Maximilien M   Lima Fabio F   Brocklehurst Cara E CE   Karaghiosoff Konstantin K   Zipse Hendrik H   Knochel Paul P  

Chemistry (Weinheim an der Bergstrasse, Germany) 20220511 33

DFT-calculations allow prediction of the reactivity of uncommon N-heterocyclic scaffolds of pyrazolo[1,5-a]pyrimidines and imidazo[1,2-b]pyridazines and considerably facilitate their functionalization. The derivatization of these N-heterocycles was realized using Grignard reagents for nucleophilic additions to 5-chloropyrazolo[1,5-a]pyrimidines and TMP<sub>2</sub> Zn ⋅ 2 MgCl<sub>2</sub>  ⋅ 2 LiCl allowed regioselective zincations. In the case of 6-chloroimidazo[1,2-b]pyridazine, bases such as T  ...[more]

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