Discovery of an in situ carbocationic system using trityl chloride as a homogeneous organocatalyst for the solvent-free condensation of β-naphthol with aldehydes and amides/thioamides/alkyl carbamates in neutral media

Ardeshir Khazaei; Mohammad Ali Zolfigol; Ahmad Reza Moosavi-Zare; Fereshteh Abi; Abdolkarim Zare; Hamideh Kaveh; Vahid Khakyzadeh; Masoud Kazem-Rostami; Abolfath Parhami; Hossein Torabi-Monfared

doi:10.1016/j.tet.2012.10.042

Discovery of an in situ carbocationic system using trityl chloride as a homogeneous organocatalyst for the solvent-free condensation of β-naphthol with aldehydes and amides/thioamides/alkyl carbamates in neutral media

Ardeshir Khazaei^*, Mohammad Ali Zolfigol, Ahmad Reza Moosavi-Zare, Fereshteh Abi, Abdolkarim Zare, Hamideh Kaveh, Vahid Khakyzadeh, Masoud Kazem-Rostami, Abolfath Parhami, Hossein Torabi-Monfared

^*Corresponding author for this work

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

84 Citations (Scopus)

Abstract

Trityl chloride (TrCl), efficiently catalyzes the one-pot multi-component condensation of β-naphthol with aromatic aldehydes and amides/thioamides/ carbamates such as acetamide, benzamide, nicotinamide, thioacetamide, and methylcarbamate under solvent-free and neutral conditions to afford 1-amido-alkyl-2-naphthols, 1-thioamido-alkyl-2-naphthols, and 1-carbamato-alkyl-2-naphthols in high yields and very short reaction times. Mechanistically, it is interesting that trityl chloride through the in situ generation of trityl carbocation with inherent instability is efficient as a reusable homogeneous organocatalyst in neutral media.

Original language	English
Pages (from-to)	212-218
Number of pages	7
Journal	Tetrahedron
Volume	69
Issue number	1
DOIs	https://doi.org/10.1016/j.tet.2012.10.042
Publication status	Published - 7 Jan 2013
Externally published	Yes

Keywords

1-Amido-alkyl-2-naphthol
1-Carbamato-alkyl-2-naphthol
1-Thioamido-alkyl-2-naphthol
Multi-component condensation
Solvent-free
Trityl chloride

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Khazaei, A., Zolfigol, M. A., Moosavi-Zare, A. R., Abi, F., Zare, A., Kaveh, H., Khakyzadeh, V., Kazem-Rostami, M., Parhami, A., & Torabi-Monfared, H. (2013). Discovery of an in situ carbocationic system using trityl chloride as a homogeneous organocatalyst for the solvent-free condensation of β-naphthol with aldehydes and amides/thioamides/alkyl carbamates in neutral media. Tetrahedron, 69(1), 212-218. https://doi.org/10.1016/j.tet.2012.10.042

@article{ea36f35a9aa344ecbc9d5baaef725c6b,

title = "Discovery of an in situ carbocationic system using trityl chloride as a homogeneous organocatalyst for the solvent-free condensation of β-naphthol with aldehydes and amides/thioamides/alkyl carbamates in neutral media",

abstract = "Trityl chloride (TrCl), efficiently catalyzes the one-pot multi-component condensation of β-naphthol with aromatic aldehydes and amides/thioamides/ carbamates such as acetamide, benzamide, nicotinamide, thioacetamide, and methylcarbamate under solvent-free and neutral conditions to afford 1-amido-alkyl-2-naphthols, 1-thioamido-alkyl-2-naphthols, and 1-carbamato-alkyl-2-naphthols in high yields and very short reaction times. Mechanistically, it is interesting that trityl chloride through the in situ generation of trityl carbocation with inherent instability is efficient as a reusable homogeneous organocatalyst in neutral media.",

keywords = "1-Amido-alkyl-2-naphthol, 1-Carbamato-alkyl-2-naphthol, 1-Thioamido-alkyl-2-naphthol, Multi-component condensation, Solvent-free, Trityl chloride",

author = "Ardeshir Khazaei and Zolfigol, \{Mohammad Ali\} and Moosavi-Zare, \{Ahmad Reza\} and Fereshteh Abi and Abdolkarim Zare and Hamideh Kaveh and Vahid Khakyzadeh and Masoud Kazem-Rostami and Abolfath Parhami and Hossein Torabi-Monfared",

year = "2013",

month = jan,

day = "7",

doi = "10.1016/j.tet.2012.10.042",

language = "English",

volume = "69",

pages = "212--218",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

number = "1",

}

Khazaei, A, Zolfigol, MA, Moosavi-Zare, AR, Abi, F, Zare, A, Kaveh, H, Khakyzadeh, V, Kazem-Rostami, M, Parhami, A & Torabi-Monfared, H 2013, 'Discovery of an in situ carbocationic system using trityl chloride as a homogeneous organocatalyst for the solvent-free condensation of β-naphthol with aldehydes and amides/thioamides/alkyl carbamates in neutral media', Tetrahedron, vol. 69, no. 1, pp. 212-218. https://doi.org/10.1016/j.tet.2012.10.042

Discovery of an in situ carbocationic system using trityl chloride as a homogeneous organocatalyst for the solvent-free condensation of β-naphthol with aldehydes and amides/thioamides/alkyl carbamates in neutral media. / Khazaei, Ardeshir; Zolfigol, Mohammad Ali; Moosavi-Zare, Ahmad Reza et al.
In: Tetrahedron, Vol. 69, No. 1, 07.01.2013, p. 212-218.

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

TY - JOUR

T1 - Discovery of an in situ carbocationic system using trityl chloride as a homogeneous organocatalyst for the solvent-free condensation of β-naphthol with aldehydes and amides/thioamides/alkyl carbamates in neutral media

AU - Khazaei, Ardeshir

AU - Zolfigol, Mohammad Ali

AU - Moosavi-Zare, Ahmad Reza

AU - Abi, Fereshteh

AU - Zare, Abdolkarim

AU - Kaveh, Hamideh

AU - Khakyzadeh, Vahid

AU - Kazem-Rostami, Masoud

AU - Parhami, Abolfath

AU - Torabi-Monfared, Hossein

PY - 2013/1/7

Y1 - 2013/1/7

N2 - Trityl chloride (TrCl), efficiently catalyzes the one-pot multi-component condensation of β-naphthol with aromatic aldehydes and amides/thioamides/ carbamates such as acetamide, benzamide, nicotinamide, thioacetamide, and methylcarbamate under solvent-free and neutral conditions to afford 1-amido-alkyl-2-naphthols, 1-thioamido-alkyl-2-naphthols, and 1-carbamato-alkyl-2-naphthols in high yields and very short reaction times. Mechanistically, it is interesting that trityl chloride through the in situ generation of trityl carbocation with inherent instability is efficient as a reusable homogeneous organocatalyst in neutral media.

AB - Trityl chloride (TrCl), efficiently catalyzes the one-pot multi-component condensation of β-naphthol with aromatic aldehydes and amides/thioamides/ carbamates such as acetamide, benzamide, nicotinamide, thioacetamide, and methylcarbamate under solvent-free and neutral conditions to afford 1-amido-alkyl-2-naphthols, 1-thioamido-alkyl-2-naphthols, and 1-carbamato-alkyl-2-naphthols in high yields and very short reaction times. Mechanistically, it is interesting that trityl chloride through the in situ generation of trityl carbocation with inherent instability is efficient as a reusable homogeneous organocatalyst in neutral media.

KW - 1-Amido-alkyl-2-naphthol

KW - 1-Carbamato-alkyl-2-naphthol

KW - 1-Thioamido-alkyl-2-naphthol

KW - Multi-component condensation

KW - Solvent-free

KW - Trityl chloride

UR - https://www.scopus.com/pages/publications/84870060880

U2 - 10.1016/j.tet.2012.10.042

DO - 10.1016/j.tet.2012.10.042

M3 - Article

AN - SCOPUS:84870060880

SN - 0040-4020

VL - 69

SP - 212

EP - 218

JO - Tetrahedron

JF - Tetrahedron

IS - 1

ER -

Discovery of an in situ carbocationic system using trityl chloride as a homogeneous organocatalyst for the solvent-free condensation of β-naphthol with aldehydes and amides/thioamides/alkyl carbamates in neutral media

Abstract

Keywords

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