Synthesis of benzotriazoles

Terpugova, M. P.; Amosov, Yu. I.; Kotlyarevskii, I. L.

doi:10.1007/bf00949965

Cited by 5 publications

(5 citation statements)

References 3 publications

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“…1083 The method requires only mild conditions, and the products are formed in excellent yields. Other copper salts, such as CuCl 2 , Cu(NO 3 ) 2 , and, surprisingly, CuSO 4 were ineffective catalysts for the reaction.…”

Section: Reactions Of Anilinesmentioning

confidence: 99%

“…A catalytic variant for the synthesis of benzotriazoles from 2-aminoazobenzenes utilizing CuCl and pyridine under oxygen was later disclosed (Scheme ) . The method requires only mild conditions, and the products are formed in excellent yields.…”

Section: Reactions Of Anilinesmentioning

confidence: 99%

“…1082 A catalytic variant for the synthesis of benzotriazoles from 2aminoazobenzenes utilizing CuCl and pyridine under oxygen was later disclosed (Scheme 528). 1083 The method requires only mild conditions, and the products are formed in excellent yields. Other copper salts, such as CuCl 2 , Cu(NO 3 ) 2 , and, surprisingly, CuSO 4 were ineffective catalysts for the reaction.…”

Section: Heterocycle Formation From Anilinesmentioning

confidence: 99%

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Aerobic Copper-Catalyzed Organic Reactions

et al. 2013

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24 peroxide [Cu I (pyr)(tpb)] 10 mol % TBHP, 1 atm O 2 , 1:2 AcOH/pyr, rt, 24 h ∼2.5 26 74 g 35 25 n-hexane aldehyde CuCl 2 , 18-crown-6 1 atm O 2 , MeCHO, CH 2 Cl 2 , 70 °C, 24 h 2.4 91 h 9 34a 26 n-decane aldehyde Cu II Cl 16 Pc-AM(PS) 3 equiv of PhCHO, MeCN, 1 atm O 2 , 50 °C 15.4 100 i 61 a See Chart 2 for ligand structures. b Also 28% cyclohexene. c Also 26% cyclohexene. d Mixture of alcohol and hydroperoxide. e Remainder of product is cyclohexene. f Approximately 93:7 of 1-adamantol/2-adamantol. g Approximately 98:2 of 1-adamantol/2-adamantol. h Afforded oxidation products in an approximately 1:1 ratio at the 2-and 3-positions. i Mixture of decanones.

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Section: Reactions Of Anilinesmentioning

confidence: 99%

Section: Reactions Of Anilinesmentioning

confidence: 99%

Section: Heterocycle Formation From Anilinesmentioning

confidence: 99%

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Aerobic Copper-Catalyzed Organic Reactions

et al. 2013

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“…Interestingly, the literature survey revealed that entire benzotriazole chemistry has been confined to construct a triazole ring over the appropriately substituted benzene ring [10][11][12][13]. We therefore deemed it interesting to attempt the construction of benzotriazoles from the preconstructed triazole ring with required substitution.…”

Section: Introductionmentioning

confidence: 99%

Junjappa‐Ila annulation: α‐Oxoketene dithioacetal mediated synthesis of substituted benzotriazoles

Shetty

Lamani

Panchamukhi

et al. 2009

Journal of Heterocyclic Chem

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in Wiley InterScience (www.interscience.wiley.com).2-(1-Benzyl-1H-1,2,3-triazole-4-yl)-3-methylsulfanyl-5-oxo-5-substituted-pent-2-enenitrile 3a-e were obtained in good yields by condensation of (1-benzyl-1H-1,2,3-triazole-4-yl)acetonitrile (1) with various a-oxoketene dithioacetals 2a-e in the presence of sodium hydride. The intermediates 3a-e underwent facile acid-induced cyclization in the presence of PTSA to afford the corresponding benzotriazoles 4a-e in moderate yields.

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“…In the former,b enzo[d]-1,2,3triazoles are N 2 -arylated with aryl halogens catalyzed by Pd, [6] Cu [7] or Fe/Cu, [8] with iodine(III) compounds with [9] or without [10] transition metal catalysts, with silyl aryl triflates, [11] and in S N Ar reactions with electron-deficient fluoroaryls. [12] In the second strategy,2 -substituteda zobenzenes or azoxybenzenes are either oxidatively or reductively cyclized.O xidatively,t his sequence has been realized with (2-tosylamino)azobenzenes [13] and 2-aminoazoxybenzenes [14] using PhI(OAc) 2 as oxidant, or by oxidizing 2-aminoazobenzenes with Cu II , [15] Cu/ Py/O 2 , [16] PhI(OAc) 2 [17] or NaOCl. [18] Substrates with ortho-N 3moiety,t hat can also be prepared in situ from suitable starting materials, are cyclized thermally [19] or by variousd ifferent reagents such as BCl 3 , [20] BF 3 , [20] Pd/TBHP, [21] and CuI/TMEDA.…”

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confidence: 99%