Reactivity of the –C(Cl)C–CN– moiety towards AlCl3-induced C–C bond forming reactions: a new synthesis of 7-(hetero)aryl-substituted pyrazolo[1,5-a]pyrimidines

Kodimuthali, Arumugam; Nishad, T. C.; Prasunamba, Padala Lakshmi; Pal, Manojit

doi:10.1016/j.tetlet.2008.11.010

Cited by 17 publications

(3 citation statements)

References 18 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Over the last twenty years, the pyrazolo[1,5-a]pyrimidine framework has been a versatile scaffold for various pharmacological studies. 3 On the other hand, during the last ten years, the pharmaceutical industry has focused on developing novel antiinflammatory agents that inhibit phosphodiesterase 4 (PDE-4) to treat chronic obstructive pulmonary disease (COPD) and asthma. 4 Recently, we have reported the usefulness of 7-(hetero)aryl-substituted pyrazolopyrimidine B (Fig.…”

mentioning

confidence: 99%

Construction of a six-membered fused N-heterocyclic ring via a new 3-component reaction: synthesis of (pyrazolo)pyrimidines/pyridines

Kumar

Mohakhud

et al. 2012

Chem. Commun.

Self Cite

View full text Add to dashboard Cite

show abstract

mentioning

confidence: 99%

Construction of a six-membered fused N-heterocyclic ring via a new 3-component reaction: synthesis of (pyrazolo)pyrimidines/pyridines

Kumar

Mohakhud

et al. 2012

Chem. Commun.

Self Cite

View full text Add to dashboard Cite

show abstract

“…Pyrazolo [1,5-a]pyrimidines precursors 2a-c and boronic acid ester 6 were synthesized according to the procedure described in the literature (Figures S1 and S2) [40,[43][44][45][46][47][48][49][50].…”

Section: Synthesis Of New Htms Py1-py3mentioning

confidence: 99%

D-π-A-Type Pyrazolo[1,5-a]pyrimidine-Based Hole-Transporting Materials for Perovskite Solar Cells: Effect of the Functionalization Position

et al. 2022

View full text Add to dashboard Cite

Donor–acceptor (D–A) small molecules are regarded as promising hole-transporting materials for perovskite solar cells (PSCs) due to their tunable optoelectronic properties. This paper reports the design, synthesis and characterization of three novel isomeric D-π-A small molecules PY1, PY2 and PY3. The chemical structures of the molecules consist of a pyrazolo[1,5-a]pyrimidine acceptor core functionalized with one 3,6-bis(4,4′-dimethoxydiphenylamino)carbazole (3,6-CzDMPA) donor moiety via a phenyl π-spacer at the 3, 5 and 7 positions, respectively. The isolated compounds possess suitable energy levels, sufficient thermal stability (Td > 400 °C), molecular glass behavior with Tg values in the range of 127–136 °C slightly higher than that of the reference material Spiro-OMeTAD (126 °C) and acceptable hydrophobicity. Undoped PY1 demonstrates the highest hole mobility (3 × 10−6 cm2 V−1 s−1) compared to PY2 and PY3 (1.3 × 10−6 cm2 V−1 s−1). The whole isomers were incorporated as doped HTMs in planar n-i-p PSCs based on double cation perovskite FA0.85Cs0.15Pb(I0.85Br0.15)3. The non-optimized device fabricated using PY1 exhibited a power conversion efficiency (PCE) of 12.41%, similar to that obtained using the reference, Spiro-OMeTAD, which demonstrated a maximum PCE of 12.58% under the same conditions. The PY2 and PY3 materials demonstrated slightly lower performance in device configuration, with relatively moderate PCEs of 10.21% and 10.82%, respectively, and slight hysteresis behavior (−0.01 and 0.02). The preliminary stability testing of PSCs is also described. The PY1-based device exhibited better stability than the device using Spiro-OMeTAD, which could be related to its slightly superior hydrophobic character preventing water diffusion into the perovskite layer.

show abstract

“…During the ongoing course of our study on the development of new methods for the synthesis of nucleoside analogues and according to reports on arylation and heteroarylation of heterocyclic systems, we had predicted that C6-aryl-substituted purine analogues could be synthesized through direct arylation of 6-chloropurine with electron-rich aromatics or heteroaromatics promoted by anhydrous AlCl 3 (Scheme , eq 3). Thus, when the reaction of 9-Bn-6-chloropurine with 1-naphthol was conducted in 1,2-dichloroethane at room temperature, the direct arylation proceeded successfully to produce the desired product 3a .…”

mentioning

confidence: 99%

Direct Synthesis of 6-Arylpurines by Reaction of 6-Chloropurines with Activated Aromatics

Guo

Niu

et al. 2010

J. Org. Chem.

View full text Add to dashboard Cite

Highly functionalized C6-aryl-substituted purine analogues were synthesized through direct arylation of 6-chloropurine with aromatics promoted by anhydrous AlCl(3) in a single step. The reactions, which were conducted using a 3-fold excess of AlCl(3) in refluxing 1,2-dichloroethane, gave moderate to excellent product yields in 0.5 h. This work is complementary to the classical coupling reactions for the synthesis of C6-aryl-substituted purine analogues.

show abstract

Reactivity of the –C(Cl)C–CN– moiety towards AlCl3-induced C–C bond forming reactions: a new synthesis of 7-(hetero)aryl-substituted pyrazolo[1,5-a]pyrimidines

Cited by 17 publications

References 18 publications

Construction of a six-membered fused N-heterocyclic ring via a new 3-component reaction: synthesis of (pyrazolo)pyrimidines/pyridines

Construction of a six-membered fused N-heterocyclic ring via a new 3-component reaction: synthesis of (pyrazolo)pyrimidines/pyridines

D-π-A-Type Pyrazolo[1,5-a]pyrimidine-Based Hole-Transporting Materials for Perovskite Solar Cells: Effect of the Functionalization Position

Direct Synthesis of 6-Arylpurines by Reaction of 6-Chloropurines with Activated Aromatics

Contact Info

Product

Resources

About