Triflic acid controlled successive annelation of aromatic sulfonamides: an efficient one-pot synthesis of N-sulfonyl pyrroles, indoles and carbazoles

Abid Shaikh; Liliana Teixeira; Béla Török

doi:10.1016/j.tetlet.2007.04.021

Triflic acid controlled successive annelation of aromatic sulfonamides: an efficient one-pot synthesis of N-sulfonyl pyrroles, indoles and carbazoles

Abid Shaikh
, Liliana Teixeira
, Béla Török

Biochemistry, Chemistry & Physics

University of Massachusetts, Amherst

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

53 Scopus citations

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Abstract

A novel one-pot synthesis of N-substituted heterocycles via successive cyclization/annelation starting from primary sulfonamides is described. This process directly leads to N-sulfonyl pyrroles, indoles and carbazoles. The selection of an appropriate reactant/triflic acid ratio successfully controls the formation of the desired product.

Original language	English
Pages (from-to)	4047-4050
Number of pages	4
Journal	Tetrahedron Letters
Volume	48
Issue number	23
DOIs	https://doi.org/10.1016/j.tetlet.2007.04.021
State	Published - Jun 4 2007

Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

Annelation
N-Heterocycles
Sulfonamides
Triflic acid

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10.1016/j.tetlet.2007.04.021

Cite this

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title = "Triflic acid controlled successive annelation of aromatic sulfonamides: an efficient one-pot synthesis of N-sulfonyl pyrroles, indoles and carbazoles",

abstract = "A novel one-pot synthesis of N-substituted heterocycles via successive cyclization/annelation starting from primary sulfonamides is described. This process directly leads to N-sulfonyl pyrroles, indoles and carbazoles. The selection of an appropriate reactant/triflic acid ratio successfully controls the formation of the desired product.",

keywords = "Annelation, N-Heterocycles, Sulfonamides, Triflic acid",

author = "Abid Shaikh and Liliana Teixeira and B{\'e}la T{\"o}r{\"o}k",

note = "Abid Shaikh, Liliana Teixeira, and B{\'e}la T{\"o}r{\"o}k. {"}Triflic Acid Controlled Successive Annelation of Aromatic Sulfonamides: An Efficient One-pot Synthesis of N-Sulfonyl Pyrroles, Indoles and Carbazoles{"} Tetrahedron Letters 48.23 (2007): 4047-4050. doi:10.1016/j.tetlet.2007.04.021 source:http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2714272/ Available at: http://works.bepress.com/abid\_shaikh/12",

year = "2007",

month = jun,

day = "4",

doi = "10.1016/j.tetlet.2007.04.021",

language = "English",

volume = "48",

pages = "4047--4050",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Triflic acid controlled successive annelation of aromatic sulfonamides

T2 - an efficient one-pot synthesis of N-sulfonyl pyrroles, indoles and carbazoles

AU - Shaikh, Abid

AU - Teixeira, Liliana

AU - Török, Béla

N1 - Abid Shaikh, Liliana Teixeira, and Béla Török. "Triflic Acid Controlled Successive Annelation of Aromatic Sulfonamides: An Efficient One-pot Synthesis of N-Sulfonyl Pyrroles, Indoles and Carbazoles" Tetrahedron Letters 48.23 (2007): 4047-4050. doi:10.1016/j.tetlet.2007.04.021 source:http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2714272/ Available at: http://works.bepress.com/abid_shaikh/12

PY - 2007/6/4

Y1 - 2007/6/4

N2 - A novel one-pot synthesis of N-substituted heterocycles via successive cyclization/annelation starting from primary sulfonamides is described. This process directly leads to N-sulfonyl pyrroles, indoles and carbazoles. The selection of an appropriate reactant/triflic acid ratio successfully controls the formation of the desired product.

AB - A novel one-pot synthesis of N-substituted heterocycles via successive cyclization/annelation starting from primary sulfonamides is described. This process directly leads to N-sulfonyl pyrroles, indoles and carbazoles. The selection of an appropriate reactant/triflic acid ratio successfully controls the formation of the desired product.

KW - Annelation

KW - N-Heterocycles

KW - Sulfonamides

KW - Triflic acid

UR - https://www.scopus.com/pages/publications/34247880138

U2 - 10.1016/j.tetlet.2007.04.021

DO - 10.1016/j.tetlet.2007.04.021

M3 - Article

SN - 0040-4039

VL - 48

SP - 4047

EP - 4050

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 23

ER -

Triflic acid controlled successive annelation of aromatic sulfonamides: an efficient one-pot synthesis of N-sulfonyl pyrroles, indoles and carbazoles

Abstract

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Keywords

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