An efficient copper(II)-catalyzed synthesis of benzothiazoles through intramolecular coupling-cyclization of N-(2-chlorophenyl)benzothioamides

E. A. Jaseer; D. J.C. Prasad; Arpan Dandapat; Govindasamy Sekar

doi:10.1016/j.tetlet.2010.07.079

An efficient copper(II)-catalyzed synthesis of benzothiazoles through intramolecular coupling-cyclization of N-(2-chlorophenyl)benzothioamides

E. A. Jaseer, D. J.C. Prasad, Arpan Dandapat, Govindasamy Sekar^*

^*Corresponding author for this work

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

92 Scopus citations

Abstract

A wide range of 2-aryl or 2-alkyl-substituted benzothiazoles are synthesized through intramolecular C_(aryl)-S bond forming-cyclization using copper(II)-BINAM-catalyzed coupling of less reactive N-(2-chlorophenyl) benzo or alkylthioamide under mild reaction conditions (82 °C).

Original language	English
Pages (from-to)	5009-5012
Number of pages	4
Journal	Tetrahedron Letters
Volume	51
Issue number	38
DOIs	https://doi.org/10.1016/j.tetlet.2010.07.079
State	Published - 2010
Externally published	Yes

Bibliographical note

Funding Information:
We thank the DST (Project No.: SR/S1/OC-06/2008), New Delhi for the financial support. E.A.J. thanks the CSIR, New Delhi and D.J.C Prasad thanks the UGC, New Delhi for SRF. We thank the DST, New Delhi for funding toward the 400-MHz NMR machine to the department of Chemistry, IIT-Madras under the IRPHA Scheme and for funding the ESI-MS facility under the FIST Program

Keywords

Benzothiazole
Copper catalyst
Coupling reaction
Diamine ligands

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2010.07.079

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title = "An efficient copper(II)-catalyzed synthesis of benzothiazoles through intramolecular coupling-cyclization of N-(2-chlorophenyl)benzothioamides",

abstract = "A wide range of 2-aryl or 2-alkyl-substituted benzothiazoles are synthesized through intramolecular C(aryl)-S bond forming-cyclization using copper(II)-BINAM-catalyzed coupling of less reactive N-(2-chlorophenyl) benzo or alkylthioamide under mild reaction conditions (82 °C).",

keywords = "Benzothiazole, Copper catalyst, Coupling reaction, Diamine ligands",

author = "Jaseer, {E. A.} and Prasad, {D. J.C.} and Arpan Dandapat and Govindasamy Sekar",

note = "Funding Information: We thank the DST (Project No.: SR/S1/OC-06/2008), New Delhi for the financial support. E.A.J. thanks the CSIR, New Delhi and D.J.C Prasad thanks the UGC, New Delhi for SRF. We thank the DST, New Delhi for funding toward the 400-MHz NMR machine to the department of Chemistry, IIT-Madras under the IRPHA Scheme and for funding the ESI-MS facility under the FIST Program ",

year = "2010",

doi = "10.1016/j.tetlet.2010.07.079",

language = "English",

volume = "51",

pages = "5009--5012",

journal = "Tetrahedron Letters",

issn = "0040-4039",

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T1 - An efficient copper(II)-catalyzed synthesis of benzothiazoles through intramolecular coupling-cyclization of N-(2-chlorophenyl)benzothioamides

AU - Jaseer, E. A.

AU - Prasad, D. J.C.

AU - Dandapat, Arpan

AU - Sekar, Govindasamy

N1 - Funding Information: We thank the DST (Project No.: SR/S1/OC-06/2008), New Delhi for the financial support. E.A.J. thanks the CSIR, New Delhi and D.J.C Prasad thanks the UGC, New Delhi for SRF. We thank the DST, New Delhi for funding toward the 400-MHz NMR machine to the department of Chemistry, IIT-Madras under the IRPHA Scheme and for funding the ESI-MS facility under the FIST Program

PY - 2010

Y1 - 2010

N2 - A wide range of 2-aryl or 2-alkyl-substituted benzothiazoles are synthesized through intramolecular C(aryl)-S bond forming-cyclization using copper(II)-BINAM-catalyzed coupling of less reactive N-(2-chlorophenyl) benzo or alkylthioamide under mild reaction conditions (82 °C).

AB - A wide range of 2-aryl or 2-alkyl-substituted benzothiazoles are synthesized through intramolecular C(aryl)-S bond forming-cyclization using copper(II)-BINAM-catalyzed coupling of less reactive N-(2-chlorophenyl) benzo or alkylthioamide under mild reaction conditions (82 °C).

KW - Benzothiazole

KW - Copper catalyst

KW - Coupling reaction

KW - Diamine ligands

UR - http://www.scopus.com/inward/record.url?scp=78549272977&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2010.07.079

DO - 10.1016/j.tetlet.2010.07.079

M3 - Article

AN - SCOPUS:78549272977

SN - 0040-4039

VL - 51

SP - 5009

EP - 5012

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 38

ER -

An efficient copper(II)-catalyzed synthesis of benzothiazoles through intramolecular coupling-cyclization of N-(2-chlorophenyl)benzothioamides

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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