Use of 2,4,6-tri-isopropylbenzenesulphonyl hydrazide in the mcfadyen-stevens aldehyde synthesis

Dudman, Christopher C.; Grice, Peter; Reese, Colin B.

doi:10.1016/0040-4039(80)80096-7

Cited by 22 publications

(2 citation statements)

References 9 publications

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“…Acyltosylhydrazides, which have functional importance as versatile building blocks in organic synthesis, are mostly prepared by common acylation of N -tosylhydrazide. , They are mainly obtained as N -acyl- N ′-tosylhydrazide 1 and are widely used as a synthetic synthon for constructing aza-aromatic rings such as tetrazoles, indazoles, pyrazoles, benzodiazepine, and so on and are frequently used as masked or protected functional groups that are easily converted to aldehydes, ,, esters, amides, and acid chloride . In particular, the conversion to aldehyde is well-known as a McFadyen−Stevens reduction .…”

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confidence: 99%

4-Aminopyridine Catalyzed Direct and Regioselective Acylation of N-Tosylhydrazide

et al. 2009

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An efficient and simple method for selective acylation of either one of two nitrogen atoms of tosylhydrazide was developed. The selectivity was drastically controlled by a catalytic amount of 4-aminopyridine or 4-(dimethylamino)pyridine with common acylating agents. The nitrogen atom masked with a tosyl group was acylated in the presence of 4-aminopyridine, whereas the primary nitrogen atom was acylated in the absence of 4-aminopyridine.

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confidence: 99%

4-Aminopyridine Catalyzed Direct and Regioselective Acylation of N-Tosylhydrazide

et al. 2009

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“…5, 143.3, 136.2, 135.8, 133.9, 130.5, 130.0, 129.2, 127.9, 127.4, 125.5, 21.0, 19.0. MS (EI) m/z = 304.1 (M + ). 14 According to the general procedure using 3-methylbenzoyl succinimide (217 mg, 1.0 mmol) and tosyl hydrazide (205 mg, 1.1 mmol), the product 3ca (207 mg, 0.68 mmol, 68% yield) was obtained as a white solid. m.p.…”

Section: N-2-methylbenzoyl-n′-tosyl Hydrazide (3ba) 2fmentioning

confidence: 99%

Synthesis of N-Acyl-N′-Sulfonyl Hydrazides from Sulfonyl Hydrazides and Activated Amides

Oh,

Lee,

2024

Synthesis

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A methodology was developed for synthesizing acyl sulfonyl hydrazides through acyl substitution reactions between activated amides and arylsulfonyl hydrazides. Optimization of the reaction conditions revealed that using Cs₂CO₃ as a base and 1,4-dioxane as a solvent at 25 °C for 12 h produced the highest yields. Among various amides tested, N-benzoylsuccinimide was found to be the most reactive, with reduced reactivity observed for N-mesityl, N-tosyl and N-Boc substituted tertiary benzoyl amides. Cross-reactions between a diverse range of N-benzoylsuccinimides and arylsulfonyl hydrazides successfully produced the corresponding N-acyl-N’-sulfonyl hydrazides with yields ranging from 63% to 93%.

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2,4,6-Triisopropylbenzenesulfonylhydrazide

Chamberlin¹,

Sheppeck²

2001

Encyclopedia of Reagents for Organic Synthesis

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Use of 2,4,6-tri-isopropylbenzenesulphonyl hydrazide in the mcfadyen-stevens aldehyde synthesis

Cited by 22 publications

References 9 publications

4-Aminopyridine Catalyzed Direct and Regioselective Acylation of N-Tosylhydrazide

4-Aminopyridine Catalyzed Direct and Regioselective Acylation of N-Tosylhydrazide

Synthesis of N-Acyl-N′-Sulfonyl Hydrazides from Sulfonyl Hydrazides and Activated Amides

2,4,6-Triisopropylbenzenesulfonylhydrazide

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