An effective BINAP and microwave accelerated palladium-catalyzed amination of 1-chloroisoquinolines in the synthesis of new 1,3-disubstituted isoquinolines

In Silico Evaluation of 1‐Aminoisoquinoline Derivatives against Dengue Virus: Greener Access via a Sonochemical Method

“…Some of the selected and relatively modern methods include (i) Cu-catalysed domino reaction of 2-alkynylbenzonitriles with secondary amines, [28] (ii) gold(III)-mediated domino reactions from 2-alkynylbenzamides and ammonium acetate [29] and (iii) Pd-catalyzed amination of 1-halo isoquinolines. [30][31][32] While these methods are known to be efficient and elegant for accessing specific 1-aminoisoquinoline derivatives, the use of expensive transition metal and their contamination with the isolated products are some of the concerns associated with these approaches. On the other hand, the traditional method for synthesizing this class of compounds include the reaction of 1-chloroisoquinolines with an amine in the presence of K 2 CO 3 in a solvent under refluxing conditions.…”

“…An initial literature search revealed that only a handful number of methods are known for the synthesis of this class of compounds. Some of the selected and relatively modern methods include (i) Cu‐catalysed domino reaction of 2‐alkynylbenzonitriles with secondary amines, [28] (ii) gold(III)‐mediated domino reactions from 2‐alkynylbenzamides and ammonium acetate [29] and (iii) Pd‐catalyzed amination of 1‐halo isoquinolines [30–32] . While these methods are known to be efficient and elegant for accessing specific 1‐aminoisoquinoline derivatives, the use of expensive transition metal and their contamination with the isolated products are some of the concerns associated with these approaches.…”

In Silico Evaluation of 1‐Aminoisoquinoline Derivatives against Dengue Virus: Greener Access via a Sonochemical Method

“…Some of the selected and relatively modern methods include (i) Cu-catalysed domino reaction of 2-alkynylbenzonitriles with secondary amines, [28] (ii) gold(III)-mediated domino reactions from 2-alkynylbenzamides and ammonium acetate [29] and (iii) Pd-catalyzed amination of 1-halo isoquinolines. [30][31][32] While these methods are known to be efficient and elegant for accessing specific 1-aminoisoquinoline derivatives, the use of expensive transition metal and their contamination with the isolated products are some of the concerns associated with these approaches. On the other hand, the traditional method for synthesizing this class of compounds include the reaction of 1-chloroisoquinolines with an amine in the presence of K 2 CO 3 in a solvent under refluxing conditions.…”

“…An initial literature search revealed that only a handful number of methods are known for the synthesis of this class of compounds. Some of the selected and relatively modern methods include (i) Cu‐catalysed domino reaction of 2‐alkynylbenzonitriles with secondary amines, [28] (ii) gold(III)‐mediated domino reactions from 2‐alkynylbenzamides and ammonium acetate [29] and (iii) Pd‐catalyzed amination of 1‐halo isoquinolines [30–32] . While these methods are known to be efficient and elegant for accessing specific 1‐aminoisoquinoline derivatives, the use of expensive transition metal and their contamination with the isolated products are some of the concerns associated with these approaches.…”

N‐Arylation of Nitrogen‐Containing Heterocycles with Cu(II) Complex of 4‐(2,2′:6′,2“‐Terpyridin‐4′‐yl)toluene as a Versatile and Efficient Catalyst

“…Several attempts have already been failed in order to extend the palladium‐catalyzed cross‐coupling methodologies to pyrazoles . In literature it has been mentioned that triazoles and tetrazoles, as more NH acidic and less nucleophilic azoles, are not suitable nucleophiles in Pd‐catalyzed C−N cross‐coupling . However, as shown in Table , N ‐arylation with 1 H ‐benzo[ d ][1,2,3]triazole in our copper catalyzed method has given moderate to good yields (entries 2, 3 and 4).…”

“…[33] In literature it has been mentioned that triazoles and tetrazoles, as more NH acidic and less nucleophilic azoles, are not suitable nucleophiles in Pd-catalyzed C À N cross-coupling. [34] However, as shown in Table 3, N-arylation with 1H-benzo[d][1,2,3]triazole in our copper catalyzed method has given moderate to good yields (entries 2, 3 and 4). As mentioned in literature [35] the arylation of 1H-benzo[d][1,2,3]triazole gives the mixture of two isomers (Table 3, entries 2 and 3).…”

Ligand-free, PdCl2(PPh3)2 catalyzed, microwave-assisted Suzuki coupling of 1-chloro-3-phenylisoquinoline in the synthesis of diversified 1,3-disubstituted isoquinolines

“…In our continued interest of isoquinolines and heterocyclics [33][34][35][36][37][38][39][40][41][42][43][44][45][46][47][48], in the present letter, the coupling of a series of boronic acid and 1-chloroisoquinoline in the synthesis of 1,3-disubstituted isoquinoline through ligand-free Suzuki coupling is reported. The reaction of 1-chloro-3-phenylisoquinoline 1 and boronic acids 2 in 1,4-dioxane in the presence of PdCl 2 (PPh 3 ) 2 catalyst and sodium carbonate base under microwave irradiation at 150 W at 110°C for 30 min afforded 1,3-disubstituted isoquinolines 3 in excellent yields and high purity (Scheme 1; Table 1).…”

In Silico Evaluation of 1‐Aminoisoquinoline Derivatives against Dengue Virus: Greener Access via a Sonochemical Method

“…Some of the selected and relatively modern methods include (i) Cu-catalysed domino reaction of 2-alkynylbenzonitriles with secondary amines, [28] (ii) gold(III)-mediated domino reactions from 2-alkynylbenzamides and ammonium acetate [29] and (iii) Pd-catalyzed amination of 1-halo isoquinolines. [30][31][32] While these methods are known to be efficient and elegant for accessing specific 1-aminoisoquinoline derivatives, the use of expensive transition metal and their contamination with the isolated products are some of the concerns associated with these approaches. On the other hand, the traditional method for synthesizing this class of compounds include the reaction of 1-chloroisoquinolines with an amine in the presence of K 2 CO 3 in a solvent under refluxing conditions.…”

“…An initial literature search revealed that only a handful number of methods are known for the synthesis of this class of compounds. Some of the selected and relatively modern methods include (i) Cu‐catalysed domino reaction of 2‐alkynylbenzonitriles with secondary amines, [28] (ii) gold(III)‐mediated domino reactions from 2‐alkynylbenzamides and ammonium acetate [29] and (iii) Pd‐catalyzed amination of 1‐halo isoquinolines [30–32] . While these methods are known to be efficient and elegant for accessing specific 1‐aminoisoquinoline derivatives, the use of expensive transition metal and their contamination with the isolated products are some of the concerns associated with these approaches.…”

N‐Arylation of Nitrogen‐Containing Heterocycles with Cu(II) Complex of 4‐(2,2′:6′,2“‐Terpyridin‐4′‐yl)toluene as a Versatile and Efficient Catalyst

“…Several attempts have already been failed in order to extend the palladium‐catalyzed cross‐coupling methodologies to pyrazoles . In literature it has been mentioned that triazoles and tetrazoles, as more NH acidic and less nucleophilic azoles, are not suitable nucleophiles in Pd‐catalyzed C−N cross‐coupling . However, as shown in Table , N ‐arylation with 1 H ‐benzo[ d ][1,2,3]triazole in our copper catalyzed method has given moderate to good yields (entries 2, 3 and 4).…”

“…[33] In literature it has been mentioned that triazoles and tetrazoles, as more NH acidic and less nucleophilic azoles, are not suitable nucleophiles in Pd-catalyzed C À N cross-coupling. [34] However, as shown in Table 3, N-arylation with 1H-benzo[d][1,2,3]triazole in our copper catalyzed method has given moderate to good yields (entries 2, 3 and 4). As mentioned in literature [35] the arylation of 1H-benzo[d][1,2,3]triazole gives the mixture of two isomers (Table 3, entries 2 and 3).…”

Ligand-free, PdCl2(PPh3)2 catalyzed, microwave-assisted Suzuki coupling of 1-chloro-3-phenylisoquinoline in the synthesis of diversified 1,3-disubstituted isoquinolines

“…In our continued interest of isoquinolines and heterocyclics [33][34][35][36][37][38][39][40][41][42][43][44][45][46][47][48], in the present letter, the coupling of a series of boronic acid and 1-chloroisoquinoline in the synthesis of 1,3-disubstituted isoquinoline through ligand-free Suzuki coupling is reported. The reaction of 1-chloro-3-phenylisoquinoline 1 and boronic acids 2 in 1,4-dioxane in the presence of PdCl 2 (PPh 3 ) 2 catalyst and sodium carbonate base under microwave irradiation at 150 W at 110°C for 30 min afforded 1,3-disubstituted isoquinolines 3 in excellent yields and high purity (Scheme 1; Table 1).…”

In Silico Evaluation of 1‐Aminoisoquinoline Derivatives against Dengue Virus: Greener Access via a Sonochemical Method

“…Some of the selected and relatively modern methods include (i) Cu-catalysed domino reaction of 2-alkynylbenzonitriles with secondary amines, [28] (ii) gold(III)-mediated domino reactions from 2-alkynylbenzamides and ammonium acetate [29] and (iii) Pd-catalyzed amination of 1-halo isoquinolines. [30][31][32] While these methods are known to be efficient and elegant for accessing specific 1-aminoisoquinoline derivatives, the use of expensive transition metal and their contamination with the isolated products are some of the concerns associated with these approaches. On the other hand, the traditional method for synthesizing this class of compounds include the reaction of 1-chloroisoquinolines with an amine in the presence of K 2 CO 3 in a solvent under refluxing conditions.…”

“…An initial literature search revealed that only a handful number of methods are known for the synthesis of this class of compounds. Some of the selected and relatively modern methods include (i) Cu‐catalysed domino reaction of 2‐alkynylbenzonitriles with secondary amines, [28] (ii) gold(III)‐mediated domino reactions from 2‐alkynylbenzamides and ammonium acetate [29] and (iii) Pd‐catalyzed amination of 1‐halo isoquinolines [30–32] . While these methods are known to be efficient and elegant for accessing specific 1‐aminoisoquinoline derivatives, the use of expensive transition metal and their contamination with the isolated products are some of the concerns associated with these approaches.…”

N‐Arylation of Nitrogen‐Containing Heterocycles with Cu(II) Complex of 4‐(2,2′:6′,2“‐Terpyridin‐4′‐yl)toluene as a Versatile and Efficient Catalyst

“…Several attempts have already been failed in order to extend the palladium‐catalyzed cross‐coupling methodologies to pyrazoles . In literature it has been mentioned that triazoles and tetrazoles, as more NH acidic and less nucleophilic azoles, are not suitable nucleophiles in Pd‐catalyzed C−N cross‐coupling . However, as shown in Table , N ‐arylation with 1 H ‐benzo[ d ][1,2,3]triazole in our copper catalyzed method has given moderate to good yields (entries 2, 3 and 4).…”

“…[33] In literature it has been mentioned that triazoles and tetrazoles, as more NH acidic and less nucleophilic azoles, are not suitable nucleophiles in Pd-catalyzed C À N cross-coupling. [34] However, as shown in Table 3, N-arylation with 1H-benzo[d][1,2,3]triazole in our copper catalyzed method has given moderate to good yields (entries 2, 3 and 4). As mentioned in literature [35] the arylation of 1H-benzo[d][1,2,3]triazole gives the mixture of two isomers (Table 3, entries 2 and 3).…”

Ligand-free, PdCl2(PPh3)2 catalyzed, microwave-assisted Suzuki coupling of 1-chloro-3-phenylisoquinoline in the synthesis of diversified 1,3-disubstituted isoquinolines

“…In our continued interest of isoquinolines and heterocyclics [33][34][35][36][37][38][39][40][41][42][43][44][45][46][47][48], in the present letter, the coupling of a series of boronic acid and 1-chloroisoquinoline in the synthesis of 1,3-disubstituted isoquinoline through ligand-free Suzuki coupling is reported. The reaction of 1-chloro-3-phenylisoquinoline 1 and boronic acids 2 in 1,4-dioxane in the presence of PdCl 2 (PPh 3 ) 2 catalyst and sodium carbonate base under microwave irradiation at 150 W at 110°C for 30 min afforded 1,3-disubstituted isoquinolines 3 in excellent yields and high purity (Scheme 1; Table 1).…”