ChemInform Abstract: P2O5/SiO2: A Simple and Effective Catalyst for the Synthesis of N‐Substituted 1‐Alkyl and 1‐Aryl 3‐Aminoisoquinolines.

Méndez, Leticia; Cánepa, Alicia S.; Rimada, Rubén S.; Bravo, Rodolfo D.

doi:10.1002/chin.201342145

Cited by 1 publication

(6 citation statements)

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“…Yield % 44, orange solid, mp: 80-81ºC; 1 C-3). The RMN data obtained for 3a are in agreement with previously reported literature values [11].…”

Section: N-(n-butyl)-1-phenylisoquinolin-3-amine (3b)supporting

confidence: 92%

“…We believe the most significant advance was the speed with which the reaction proceeded under microwave conditions. The optimal reaction yield of 40% ( Table 1, entry 3) obtained after 40 minutes, was significantly lower than that obtained via conventional method (120 hours), although the latter performance yield was slightly higher, i.e, 48% [11]. No increase in performance yield was observed at longer reaction times under microwave conditions (entries 4 and 5).…”

Section: Resultsmentioning

confidence: 88%

“…The yields of the reactions are summarized in Table 2. All products are known compounds and were identified by comparison of their physical and spectroscopic data with those of reported ones [10,11]. Assignments of carbon resonance were performed using both 1D and 2D NMR (COSY) and heteronuclear 1 H/ 13 C (HSQC and HMBC) experiments.…”

Section: Resultsmentioning

confidence: 99%

“…More recently, we studied the reaction using P 2 O 5 /SiO 2 and HClO 4 /SiO 2 as heterogeneous catalysts as eco-friendly alternatives. The results indicate that both catalysts are efficient for the reaction with similar yields [11]. However, P 2 O 5 /SiO 2 demonstrated to have a much better performance: a minor amount of catalyst was needed; it showed greater selectivity as well as a lower formation of byproducts than HClO 4 /SiO 2 .…”

Section: Introductionmentioning

confidence: 84%

“…The progress of the reaction was monitored by TLC. After completion of the reaction, the resulting yellow solid was washed three times with hexane/ethyl acetate (7:3) to [10] 3b Ph n-Bu 44 164-165/164-166 [11] 3c Ph Me 52 142-143/142-144 [10] 3d Ph p-Cl-Ph 34 192-194/192-193 [11] 3e Me Me 77 80-81/81-82 [11] 3f Me n-Bu 59 123-124/123-124.5 [11] 3g Me Ph 51 63-64/63-64 [11] 3h Me p-Tolyl 48 87-88/88-89 [11] remove unreacted reagent accompanied by a small percentage of impurities. The reactions carried out with catalyst are performed in the same way.…”

Section: General Procedures For the Preparation Of N1-substituted Isomentioning

confidence: 99%

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Microwave-induced Synthesis of N-Substituted 1-Alkyl and 1-Aryl 3-Aminoisoquinolines

Méndez¹,

Villalba²,

Cánepa

et al. 2017

LOC

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Background: Aminoisoquinolines are an important class of heterocyclic compounds. These compounds present a wide range of pharmacological properties including antimalaric, anticonvulsant and anti-inflammatory. Although several preparation routes may be found in the literature for the preparation of these compounds, many of these methods present difficulties, including laborious isolation methods, drastic conditions and extended reaction times. Methods: The synthesis of N-substituted 1-alkyl and 1-aryl-3-aminoisoquinolines is developed through the reaction of 2-acylphenylacetonitriles with amines under microwave irradiation conditions. The reactions were performed in ethanol as a solvent without the use of catalyst. In parallel, these reactions were performed under identical conditions of temperature using P 2 O 5 /SiO 2 as a catalyst in different amounts. Results: A series of N-substituted 1-alkyl and 1-aryl-3-aminoisoquinolines were synthesized using microwave irradiation with as high selectivity, short reaction times and without the use of catalyst. The use of P 2 O 5 /SiO 2 as catalyst under microwave irradiation conditions was not effective for these reactions. Conclusion: The results show an efficient method for the synthesis of N-substituted 1-alkyl and 1-aryl-3-aminoisoquinolines by the reaction of 2-acylphenylacetonitriles with amines using microwave irradiation. Some important advantages for this method include a strong decrease in reaction time, a good selectivity, and the absence of catalyst, with simplicity in operation and a benefit to the environment.

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“…Yield % 44, orange solid, mp: 80-81ºC; 1 C-3). The RMN data obtained for 3a are in agreement with previously reported literature values [11].…”

Section: N-(n-butyl)-1-phenylisoquinolin-3-amine (3b)supporting

confidence: 92%

Section: Resultsmentioning

confidence: 88%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 84%

Section: General Procedures For the Preparation Of N1-substituted Isomentioning

confidence: 99%

See 3 more Smart Citations

Microwave-induced Synthesis of N-Substituted 1-Alkyl and 1-Aryl 3-Aminoisoquinolines

Méndez¹,

Villalba²,

Cánepa

et al. 2017

LOC

View full text Add to dashboard Cite

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ChemInform Abstract: P₂O₅/SiO₂: A Simple and Effective Catalyst for the Synthesis of N‐Substituted 1‐Alkyl and 1‐Aryl 3‐Aminoisoquinolines.

Cited by 1 publication

References 1 publication

Microwave-induced Synthesis of N-Substituted 1-Alkyl and 1-Aryl 3-Aminoisoquinolines

Microwave-induced Synthesis of N-Substituted 1-Alkyl and 1-Aryl 3-Aminoisoquinolines

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