Catalyst-free, one-pot expeditious synthesis of polyhydroquinolines and 2-amino-4H-chromenes

Ganwir, Prerna; Bandivadekar, Priyanka; Kudale, Pawan; Chaturbhuj, Ganesh U.

doi:10.1007/s11164-022-04763-0

Cited by 3 publications

(10 citation statements)

References 69 publications

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“…275–277°C (lit. 21 277–278°C); 1 H NMR (500 MHz, DMSO‐d6) δ 12.68 (s, 1H), 8.08 (d, J = 7.2 Hz, 2H), 7.57–7.40 (m, 8H), 7.36 (t, J = 7.3 Hz, 2H), 7.29 (t, J = 7.6 Hz, 2H), 7.21 (t, J = 7.3 Hz, 1H).…”

Section: Methodsmentioning

confidence: 99%

“…265–268°C (lit. 21 265–267°C); 1 H NMR (400 MHz, DMSO‐d6) δ 12.43 (s, 1H), 9.77 (s, 1H), 7.91 (d, J = 8.6 Hz, 2H), 7.59–7.14 (m, 10H), 6.86 (d, J = 8.7 Hz, 2H).…”

Section: Methodsmentioning

confidence: 99%

“…: 218–221°C (lit. 21 218–220°C); 1 H NMR (400 MHz, DMSO‐d6) δ 12.46 (s, 1H), 7.98 (d, J = 8.9 Hz, 2H), 7.56–7.13 (m, 10H), 7.01 (d, J = 8.8 Hz, 2H), 3.78 (s, 3H).…”

Section: Methodsmentioning

confidence: 99%

“…233–236°C (lit. 21 233–235°C); 1 H NMR (400 MHz, DMSO‐d6) δ 13.14 (s, 1H), 8.64 (t, J = 6.2 Hz, 1H), 8.16 (d, J = 7.9 Hz, 1H), 7.96–7.88 (m, 1H), 7.59–7.21 (m, 11H).…”

Section: Methodsmentioning

confidence: 99%

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Catalyst‐free one‐pot synthesis of 2,4,5‐tri‐ and 1,2,4,5‐tetrasubstituted imidazoles

Bandivadekar,

Chaturbhuj

2023

Journal of Heterocyclic Chem

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The present work emphasizes catalyst‐free 2,4,5‐tri‐ and 1,2,4,5‐tetra substituted imidazole synthesis using diversified aldehydes with benzil, ammonium acetate, or amines. Ammonium acetate plays a vital role as a reactant catalyst by dissociating into acetic acid to afford imine and diamine formation to ascertain the 2,4,5‐tri‐ and 1,2,4,5‐tetra substituted imidazoles. The key advantages of the current approach are efficient, greener, eco‐friendly, and facile, with moderate to excellent yield in shorter reaction time at the temperature of 80°C. Ethanol:water as a solvent makes the reaction process eco‐friendly. Overall, the described approach offers a promising route for the efficient and sustainable synthesis of substituted imidazoles, which have a wide range of applications in various fields, including pharmaceuticals, agrochemicals, and materials science.

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Section: Methodsmentioning

confidence: 99%

“…265–268°C (lit. 21 265–267°C); 1 H NMR (400 MHz, DMSO‐d6) δ 12.43 (s, 1H), 9.77 (s, 1H), 7.91 (d, J = 8.6 Hz, 2H), 7.59–7.14 (m, 10H), 6.86 (d, J = 8.7 Hz, 2H).…”

Section: Methodsmentioning

confidence: 99%

“…: 218–221°C (lit. 21 218–220°C); 1 H NMR (400 MHz, DMSO‐d6) δ 12.46 (s, 1H), 7.98 (d, J = 8.9 Hz, 2H), 7.56–7.13 (m, 10H), 7.01 (d, J = 8.8 Hz, 2H), 3.78 (s, 3H).…”

Section: Methodsmentioning

confidence: 99%

“…233–236°C (lit. 21 233–235°C); 1 H NMR (400 MHz, DMSO‐d6) δ 13.14 (s, 1H), 8.64 (t, J = 6.2 Hz, 1H), 8.16 (d, J = 7.9 Hz, 1H), 7.96–7.88 (m, 1H), 7.59–7.21 (m, 11H).…”

Section: Methodsmentioning

confidence: 99%

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Catalyst‐free one‐pot synthesis of 2,4,5‐tri‐ and 1,2,4,5‐tetrasubstituted imidazoles

Bandivadekar,

Chaturbhuj

2023

Journal of Heterocyclic Chem

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“…In that study, the reaction proceeds smoothly and only trace amounts of the corresponding heterocyclic product had been obtained. 43 After the optimization, the scope of the aryl aldehydes was investigated (Table 2). Different substituted benzaldehydes were subjected to the optimized reaction conditions.…”

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confidence: 99%

Three-Component Synthesis of Tetrahydrobenzo[b]pyrans Catalyzed by Sodium Cyclamate

Kiyani¹,

Baghaie²

2022

HETEROCYCLES

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The one-pot three-component cyclocondensation for the synthesis of tetrahydrobenzo [b]pyran derivatives in the presence of sodium cyclamate has been investigated. The three-component reaction was carried out in water medium under refluxing condition. Screening the reaction conditions revealed that 20 mol% sodium cyclamate refluxing water afforded the best results. Under green conditions, different substituted tetrahydrobenzo[b]pyrans were obtained from simple available starting materials, including malononitrile, functionalized benzaldehydes, and dimedone, via using an established efficient and straightforward approach.Multicomponent reactions (MCRs) involve at least three reactants that reacted in one-pot approach to synthesize valuable organic compounds and pharmacologically active molecules with high complexity and diversity as well as minimum side reactions. Green bond-forming, atomic and structural economy, step economy, high bond-forming index, avoidance of complicated purification processes and separation of intermediates, time-saving, mild conditions, environmental friendliness, elimination of waste production, energy-saving, and excellent functional group compatibility are the merits of MCRs. 1 In this reason, MCRs have been used for the synthesis of various heterocyclic compounds. 2 Tetrahydrobenzo[b]pyran derivatives are one of the biologically scaffolds owing to their applications in the synthetic and medicinal chemistry. 3 These important oxygen-containing heterocyclic compounds exhibit bioactivities, including anti-coagulant, 3 anti-anaphylactic, 3 calcium antagonist, 3 anticancer, 4 antibacterial, 5 anti-inflammatory, 6 lactamase inhibitor, 7 antifungal, 8 antioxidant, 8 anti-Huntington, anti-Alzheimer, anti-Schizophrenia, and anti-Parkinson. 3,9 The structures of some biologically active tetrahydrobenzo [b]pyrans are depicted in Figure 1. Besides, tetrahydrobenzo[b]pyrans were applied as starting materials to synthesize spirocyclopropylbarbiturates, 10 spirocyclopropylpyrazolones,

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Copper Slag as efficient catalyst for the Fenton-like reaction: Conversion of alcohols to carbonyls

Savale,

Bandivadekar,

Chaturbhuj

2024

Tetrahedron Letters

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Catalyst-free, one-pot expeditious synthesis of polyhydroquinolines and 2-amino-4H-chromenes

Cited by 3 publications

References 69 publications

Catalyst‐free one‐pot synthesis of 2,4,5‐tri‐ and 1,2,4,5‐tetrasubstituted imidazoles

Catalyst‐free one‐pot synthesis of 2,4,5‐tri‐ and 1,2,4,5‐tetrasubstituted imidazoles

Three-Component Synthesis of Tetrahydrobenzo[b]pyrans Catalyzed by Sodium Cyclamate

Copper Slag as efficient catalyst for the Fenton-like reaction: Conversion of alcohols to carbonyls

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