Benzotriazole-Mediated Synthesis of N-Alkyl-N,n′-Diarylhydrazines

Katritzky, Alan R.; Verin, S. V.; Yang, Baozhen

doi:10.1080/00304949609355912

Cited by 5 publications

(5 citation statements)

References 7 publications

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“…α-Benzotriazolyl carbanions 713 add to azobenzenes to form the N -benzotriazol-1-ylalkyl phenylhydrazines 714 , which react in situ with Grignard reagents to give the corresponding trisubstituted hydrazines 715 in moderate yields (Scheme , Table ) 225 Addition of Lithiated N -Substituted Benzotriazoles to Azobenzenes 75 Preparation of 1,1,2-Trisubstituted Hydrazines 715 RR 1 Aryield % H n -Bu Ph 34 CHCH 2 n -Bu Ph 32 Ph Me Ph 40 Ph n -Bu Ph 54 Ph n -Bu 4-ClC 6 H 4 51 Ph n -Bu 4-MeC 6 H 4 48 Ph Ph Ph 52 4-MeC 6 H 4 n -Bu Ph 57

…”

Section: From Systems Of Type Bt−c−n By C- and H-nucleophiles: Amino...mentioning

confidence: 99%

“…200 Addition of the anion 265 to azobenzenes produces the unstable intermediates 274, which upon trapping with Grignard reagent and subsequent hydrolysis give unsymmetrical trisubstituted hydrazines 275 (see also section IV.B.1.g). 201 Hydroxybenzyl groups, as in (benzotriazolylmethyl)phenols, prevent the formation of the desired carbanion due to deactivation of the methylene hydrogens and formation of the low-solubility phenoxide ion. However, the lithiation succeeds in good overall yields using a one-pot reaction, employing the easily removable trimethylsilyl protecting group 131,202,203,257 (Scheme 97, Table 30).…”

Section: Bt−ch−arylmentioning

confidence: 99%

“…59 N-(3-Benzotriazolyl-3-amidopropyl)-substituted monoaza- 102 and diaza-124 crown ethers are reduced with lithium aluminum hydride in refluxing THF to give N-(3-aminopropyl) macrocycles 650 and 651, respectively (Scheme 201). However, a carbazolyl moiety in the R position to benzotriazolyl group 201). Tertiary amines 655 with two identical N substituents can be prepared from the benzotriazole condensation products derived from a primary amine by reactions with a Grignard reagent.…”

Section: From Systems Of Type Bt−c−n By C-and H-nucleophiles: Aminoal...mentioning

confidence: 99%

“…R-Benzotriazolyl carbanions 713 add to azobenzenes to form the N-benzotriazol-1-ylalkyl phenylhydrazines 714, which react in situ with Grignard reagents to give the corresponding trisubstituted hydrazines 715 in moderate yields (Scheme 225, Table 75). 201…”

Section: E With Grignards and With Methylenetriphenylphosphorane To G...mentioning

confidence: 99%

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Properties and Synthetic Utility ofN-Substituted Benzotriazoles

et al. 1998

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Section: From Systems Of Type Bt−c−n By C- and H-nucleophiles: Amino...mentioning

confidence: 99%

Section: Bt−ch−arylmentioning

confidence: 99%

Section: From Systems Of Type Bt−c−n By C-and H-nucleophiles: Aminoal...mentioning

confidence: 99%

Section: E With Grignards and With Methylenetriphenylphosphorane To G...mentioning

confidence: 99%

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Properties and Synthetic Utility ofN-Substituted Benzotriazoles

et al. 1998

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“…We now report new preparations of (i) trisubstituted hydrazines in high yields by the reactions of N -(1-benzotriazolylalkyl)- N,N‘ -disubstituted hydrazines with Grignard reagents or organozinc reagents and (ii) substituted pyrazolidines by the reactions of N -(1-benzotriazolylalkyl)- N,N‘ -diarylhydrazines with electron-rich alkenes. We recently reported the preparation of trisubstituted and tetrasubstituted hydrazines in yields of 32−57% by additions of α-lithio-1-alkylbenzotriazoles to the NN bond of azobenzenes, followed by substitution of the benzotriazole residue by Grignard reagents …”

Section: Introductionmentioning

confidence: 99%

Preparations of Trisubstituted Hydrazines and Pyrazolidines from N-(1-Benzotriazolylalkyl)hydrazines

1997

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Reactions of N,N'-disubstituted hydrazines with benzotriazole and aldehydes give N-(alpha-benzotriazoylalkyl)-N,N'-disubstituted hydrazines which on treatment with organometallic reagents form N-alkyl-N,N'-disubstituted hydrazines in good yields. N-(Benzotriazolylalkyl)-N,N'-disubstituted hydrazines and electron-rich olefins, in the presence of zinc bromide catalyst, generate N,N'-disubstituted pyrazolidines in moderate to good yields.

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Electrophilic Amination of Carbanions, Enolates, and Their Surrogates

Ciganek

2009

Organic Reactions

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This chapter deals with the formation of carbon‐nitrogen bonds by reaction of carbon nucleophiles with electrophilic aminating reagents. The former encompass aliphatic and aromatic carbanions, enolates and their surrogates such as enamines, enol esters, and enol ethers, as well as carbanions stabilized by cyano or sulfone groups or by phosphorus. A section entitled Reagents and Mechanisms lists the many aminating reagents available and discusses the mechanisms by which the more important ones react. Among the electrophiles discussed are halo amines, various hydroxylamine derivatives, oxaziridines, imines, oximes, diazonium salts, diazo compounds, azo compounds, and azides. The section on Scope and Limitations is organized by carbon nucleophiles and attempts to suggest the best reagents for each class. A number of electrophilic aminating reagents that have been omitted from the scope of this chapter are briefly discussed, with references to reviews, in the section on Comparison with Other Methods. Tables listing references to the preparation of the various aminating reagents are found in the section on Experimental Conditions. References to the conversion of non‐amine products into amines are also provided there. The literature is covered to the middle of 2007.

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Benzotriazole-Mediated Synthesis of N-Alkyl-N,n′-Diarylhydrazines

Cited by 5 publications

References 7 publications

Properties and Synthetic Utility ofN-Substituted Benzotriazoles

Properties and Synthetic Utility ofN-Substituted Benzotriazoles

Preparations of Trisubstituted Hydrazines and Pyrazolidines from N-(1-Benzotriazolylalkyl)hydrazines

Electrophilic Amination of Carbanions, Enolates, and Their Surrogates

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