Highly efficient synthesis of capsaicin analogues by condensation of vanillylamine and acyl chlorides in a biphase H2O/CHCl3 system

Bo Wang; Fan Yang; Yi Fan Shan; Wen Wei Qiu; Jie Tang

doi:10.1016/j.tet.2009.04.046

Highly efficient synthesis of capsaicin analogues by condensation of vanillylamine and acyl chlorides in a biphase H₂O/CHCl₃ system

Bo Wang
, Fan Yang
, Yi Fan Shan
, Wen Wei Qiu^*
, Jie Tang

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China Normal University

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

22 Scopus citations

Abstract

Highly efficient synthesis of capsaicin analogues was developed using condensation of vanillylamine with acyl chlorides in a biphase H₂O/CHCl₃ system under mild conditions. For C4-C18 aliphatic or aromatic acyl chlorides, the yields were up to 93-96% with high purity after a simple work-up procedure, and only 1-1.16 equiv of acyl chloride was needed in the reaction.

Original language	English
Pages (from-to)	5409-5412
Number of pages	4
Journal	Tetrahedron
Volume	65
Issue number	27
DOIs	https://doi.org/10.1016/j.tet.2009.04.046
State	Published - 4 Jul 2009

Keywords

Acylation
Capsaicin analogue
Vanillylamine

Access to Document

10.1016/j.tet.2009.04.046

Cite this

@article{e3b463713d6b404a84c7c4786f984177,

title = "Highly efficient synthesis of capsaicin analogues by condensation of vanillylamine and acyl chlorides in a biphase H2O/CHCl3 system",

abstract = "Highly efficient synthesis of capsaicin analogues was developed using condensation of vanillylamine with acyl chlorides in a biphase H2O/CHCl3 system under mild conditions. For C4-C18 aliphatic or aromatic acyl chlorides, the yields were up to 93-96\% with high purity after a simple work-up procedure, and only 1-1.16 equiv of acyl chloride was needed in the reaction.",

keywords = "Acylation, Capsaicin analogue, Vanillylamine",

author = "Bo Wang and Fan Yang and Shan, \{Yi Fan\} and Qiu, \{Wen Wei\} and Jie Tang",

year = "2009",

month = jul,

day = "4",

doi = "10.1016/j.tet.2009.04.046",

language = "英语",

volume = "65",

pages = "5409--5412",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "27",

}

TY - JOUR

T1 - Highly efficient synthesis of capsaicin analogues by condensation of vanillylamine and acyl chlorides in a biphase H2O/CHCl3 system

AU - Wang, Bo

AU - Yang, Fan

AU - Shan, Yi Fan

AU - Qiu, Wen Wei

AU - Tang, Jie

PY - 2009/7/4

Y1 - 2009/7/4

N2 - Highly efficient synthesis of capsaicin analogues was developed using condensation of vanillylamine with acyl chlorides in a biphase H2O/CHCl3 system under mild conditions. For C4-C18 aliphatic or aromatic acyl chlorides, the yields were up to 93-96% with high purity after a simple work-up procedure, and only 1-1.16 equiv of acyl chloride was needed in the reaction.

AB - Highly efficient synthesis of capsaicin analogues was developed using condensation of vanillylamine with acyl chlorides in a biphase H2O/CHCl3 system under mild conditions. For C4-C18 aliphatic or aromatic acyl chlorides, the yields were up to 93-96% with high purity after a simple work-up procedure, and only 1-1.16 equiv of acyl chloride was needed in the reaction.

KW - Acylation

KW - Capsaicin analogue

KW - Vanillylamine

UR - https://www.scopus.com/pages/publications/66149102853

U2 - 10.1016/j.tet.2009.04.046

DO - 10.1016/j.tet.2009.04.046

M3 - 文章

AN - SCOPUS:66149102853

SN - 0040-4020

VL - 65

SP - 5409

EP - 5412

JO - Tetrahedron

JF - Tetrahedron

IS - 27

ER -

Highly efficient synthesis of capsaicin analogues by condensation of vanillylamine and acyl chlorides in a biphase H₂O/CHCl₃ system

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this