One-carbon homologation of aldehydes to N-(α-haloacyl)benzotriazoles

Alan R. Katritzky; Srinivasa R. Tala; Sandeep K. Singh

doi:10.1055/s-2006-950183

One-carbon homologation of aldehydes to N-(α-haloacyl)benzotriazoles

Alan R. Katritzky, Srinivasa R. Tala, Sandeep K. Singh

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

Abstract

One-carbon homologated N-(α-haloacyl)benzotriazoles have been synthesized from the corresponding aromatic and aliphatic aldehydes. Vinylbenzotriazoles, prepared by the reaction of aldehydes with the one-carbon synthon BtCH₂P⁺Ph₃Cl^-, were subsequently treated with Br₂/Et₃N to give 1-bromovinylbenzotriazoles. These were then treated with NBS/NIS in CH ₃CN-H₂O to furnish one-carbon homologated N-(α-haloacyl)benzotriazoles in 53-77% yields. We have also demonstrated the utility of these new reagents in organic synthesis.

Original language	English (US)
Pages (from-to)	3231-3237
Number of pages	7
Journal	Synthesis
Issue number	19
DOIs	https://doi.org/10.1055/s-2006-950183
State	Published - Oct 4 2006
Externally published	Yes

Keywords

Acylation
Aldehyde
Homologation
N-acylbenzotriazole
N-halosuccinimide

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10.1055/s-2006-950183

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title = "One-carbon homologation of aldehydes to N-(α-haloacyl)benzotriazoles",

abstract = "One-carbon homologated N-(α-haloacyl)benzotriazoles have been synthesized from the corresponding aromatic and aliphatic aldehydes. Vinylbenzotriazoles, prepared by the reaction of aldehydes with the one-carbon synthon BtCH2P+Ph3Cl-, were subsequently treated with Br2/Et3N to give 1-bromovinylbenzotriazoles. These were then treated with NBS/NIS in CH 3CN-H2O to furnish one-carbon homologated N-(α-haloacyl)benzotriazoles in 53-77% yields. We have also demonstrated the utility of these new reagents in organic synthesis.",

keywords = "Acylation, Aldehyde, Homologation, N-acylbenzotriazole, N-halosuccinimide",

author = "Katritzky, {Alan R.} and Tala, {Srinivasa R.} and Singh, {Sandeep K.}",

year = "2006",

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doi = "10.1055/s-2006-950183",

language = "English (US)",

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journal = "Synthesis",

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TY - JOUR

T1 - One-carbon homologation of aldehydes to N-(α-haloacyl)benzotriazoles

AU - Katritzky, Alan R.

AU - Tala, Srinivasa R.

AU - Singh, Sandeep K.

PY - 2006/10/4

Y1 - 2006/10/4

N2 - One-carbon homologated N-(α-haloacyl)benzotriazoles have been synthesized from the corresponding aromatic and aliphatic aldehydes. Vinylbenzotriazoles, prepared by the reaction of aldehydes with the one-carbon synthon BtCH2P+Ph3Cl-, were subsequently treated with Br2/Et3N to give 1-bromovinylbenzotriazoles. These were then treated with NBS/NIS in CH 3CN-H2O to furnish one-carbon homologated N-(α-haloacyl)benzotriazoles in 53-77% yields. We have also demonstrated the utility of these new reagents in organic synthesis.

AB - One-carbon homologated N-(α-haloacyl)benzotriazoles have been synthesized from the corresponding aromatic and aliphatic aldehydes. Vinylbenzotriazoles, prepared by the reaction of aldehydes with the one-carbon synthon BtCH2P+Ph3Cl-, were subsequently treated with Br2/Et3N to give 1-bromovinylbenzotriazoles. These were then treated with NBS/NIS in CH 3CN-H2O to furnish one-carbon homologated N-(α-haloacyl)benzotriazoles in 53-77% yields. We have also demonstrated the utility of these new reagents in organic synthesis.

KW - Acylation

KW - Aldehyde

KW - Homologation

KW - N-acylbenzotriazole

KW - N-halosuccinimide

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U2 - 10.1055/s-2006-950183

DO - 10.1055/s-2006-950183

M3 - Article

AN - SCOPUS:33750083039

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EP - 3237

JO - Synthesis

JF - Synthesis

IS - 19

ER -

One-carbon homologation of aldehydes to N-(α-haloacyl)benzotriazoles

Abstract

Keywords

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