Solvent- and catalyst-free direct reductive amination of aldehydes and ketones with Hantzsch ester: synthesis of secondary and tertiary amines

Nguyen, Quynh Pham Bao; Kim, Taek Hyeon

doi:10.1016/j.tet.2013.04.046

Cited by 21 publications

(9 citation statements)

References 29 publications

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“…The target product was prepared in 99 % yield at 150 °C using 5Å molecular sieves as an additive. [ 185 ]…”

Section: Trialkylamines Synthesismentioning

confidence: 99%

“…The target product was prepared in 99 % yield at 150°C using 5Å molecular sieves as an additive. [185] In 2006 Suginome and co-authors reported a new approach for the reductive amination using NaBH 4 as a reducing agent. To facilitate the intermediate iminium ion formation authors added 1 equivalent of aminoborane reagent.…”

Section: Scheme 63 Synthesis Of Oxyquinoline Tripodal Ligandmentioning

confidence: 99%

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Symmetrical Tertiary Amines: Applications and Synthetic Approaches

et al. 2020

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“…The target product was prepared in 99 % yield at 150 °C using 5Å molecular sieves as an additive. [ 185 ]…”

Section: Trialkylamines Synthesismentioning

confidence: 99%

Section: Scheme 63 Synthesis Of Oxyquinoline Tripodal Ligandmentioning

confidence: 99%

Symmetrical Tertiary Amines: Applications and Synthetic Approaches

et al. 2020

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“…Teknik mikrogelombang menghasilkan pemanasan dalaman yang lebih cekap disebabkan tenaga gelombang mikronya selari dengan molekul-molekul pelarut dan reagen yang terlibat dalam tindak balas. Maka masa tindak balas menjadi lebih cepat [7]. Jadual di atas membuktikan bahawa peratusan hasil daripada kaedah mikrogelombang adalah lebih tinggi berbanding dengan kaedah refluks.…”

Section: Keputusan Dan Perbincanganunclassified

“…Sintesis ini mengambil masa dua jam hingga semalaman [2]. Penggunaan mikrogelombang ini juga dikaitkan dengan konsep 'Kimia Hijau' kerana kaedah ini menggunakan tenaga mikrogelombang untuk tindak balas kimia [7]. Pada tahun 2012, satu kajian untuk sintesis sebatian N-fenil-4-(6-fenilimidazo[2,1-b]tiazol-5-il)tiazol-2-amina turut menggunakan kaedah mikrogelombang [8].…”

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Penggunaan Kaedah Penyinaran Mikrogelombang Dalam Sintesis Terbitan Tiourea

Ahyak¹,

Rohadi²,

Ngah³

et al. 2016

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AbstrakSebatian baru terbitan tiourea, 1-etil-1-(2-hidroksi-etil)-3-naftalen-1-il-tiourea (3a) dan 1-(fenil-amino)-3-naftalen-1-il-tiourea (3b) telah berjaya disintesis melalui tindak balas antara 1-naftil isotiosianat (1) dengan etilena 2-etilaminoetanol (2a) dan fenilhidrazina (2b) menggunakan kaedah penyinaran mikrogelombang dan kaedah refluks. Peratusan hasil bagi kedua-dua kaedah yang digunakan untuk sebatian 3a dan 3b masing-masing adalah 3a (refluks: 66%, mikrogelombang: 98%) dan 3b (refluks: 72%, mikrogelombang: 97%). Hasil sintesis dianalisa dengan menggunakan alat spektroskopi FT-Inframerah (FT-IM), Spektroskopi Resonan Magnetik Nuklear (RMN) dan Spektrometri Jisim. Kajian antimikrob juga dilakukan dengan menggunakan Staphylococcus aureus dan Bacillus subtillus sebagai Gram positif, Escherichia coli dan Salmonella typhimurium sebagai Gram negatif dan kulat yang digunakan adalah Aspergillus niger. Kawalan positif yang digunakan adalah streptomisin dan kanamisin, manakala kawalan negatif yang digunakan adalah DMSO. Walaubagaimanapun hasil kajian mendapati tiada perencatan yang ketara terhadap pertumbuhan bakteria dan kulat (hanya 6-7mm kawasan perencatan) menggunakan sebatian tiourea ini.Kata kunci: sebatian tiourea, mikrogelombang, aktiviti antimikrob Abstract New thiourea derivatives, 1-ethyl-1-(2-hydroxy-ethyl)-3-naphthalen-1-yl-iourea (3a), 1-(phenyl-amino)-3-naphthalen-1-ylTiourea (3b) have been synthesized from the reaction of naphthylisothiocyanate with 2-(ethylamino)ethanol (2a) and phenylhydrazine (2b) using microwave irradiation method. The percentage yield for both method used for compound 3a and 3b, respectively 3a (reflux: 66%, microwave: 98%) and 3b (refluks: 72%, mikrogelombang: 97%).The compounds were analyzed by using Spectrometer FT-Infrared (FT-IR), Spectrometer Nuclear Magnetic Resonance (NMR) and Mass Spectrometry. Antimicrobial study was also conducted using Staphylococcus aureus and Bacillus subtillus as Gram positive, Escherichia coli and Salmonella typhimurium as Gram negative and fungi Aspergillus niger is used. The positive control used was streptomycin and kanamycin, while DMSO was used as the negative. However, this study shows no inhibition of bacteria and fungi (6-7mm of inhibition area) using these thiourea compounds.Keywords: thiourea compound, microvawe, antimicrob activity Pengenalan Tiourea adalah sebatian organosulfur yang mempunyai formula SC(NH 2 ) 2 . Struktur molekulnya sama seperti urea kecuali kedudukan oksigen digantikan dengan sulfur. Dalam satu kajian terbitan tiourea, kompleks poli(etilena

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“…[5][6][7] Direct reductive amination of carbonyl compounds remain the simplest approach. [8][9][10] Typically, reductive amination of aldehydes or ketones, in which a mixture of a carbonyl compound and an amine is treated with a reductant in a "one-pot" fashion, is one of the most useful methods for the preparation of secondary or tertiary amines which avoids the isolation of an unstable imine or iminium intermediate. [11][12][13] As shown in Scheme 1, one of the synthetic methods to N-benzyl-N-phenylamines 3 utilized condensation between aldehydes 1 and anilines 2 followed by reduction of the imine intermediate 4.…”

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confidence: 99%