Iodine-Promoted Cascade Redox Cyclization to Access 2-Arylbenzothiazoles Using Elemental Sulfur

Yakkanti Chiranjeevi; Sujeet Gaware; Rana Chatterjee; Jayshree Solanke; Rapolu Venkateshwarlu; L.  Vaikunta Rao; Gorle Simhachalam; Rambabu Dandela

doi:10.1002/jhet.4902

Iodine-Promoted Cascade Redox Cyclization to Access 2-Arylbenzothiazoles Using Elemental Sulfur

Yakkanti Chiranjeevi, Sujeet Gaware, Rana Chatterjee, Jayshree Solanke, Rapolu Venkateshwarlu, L. Vaikunta Rao, Gorle Simhachalam, Rambabu Dandela

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

1 Scopus citations

Abstract

A straightforward and efficient method has been developed to access a variety of benzothiazole derivatives via cascade reductive annulation. Iodine mediated, one-pot three-component reaction of o-chloronitroarenes, aryl aldehydes, and elemental sulfur effectively produce benzothiazoles. Moreover, the metal-free strategy allows the facile synthesis of diverse 2-substituted benzothiazoles through multiple carbon–heteroatom bonds in good yields. The present protocol features a greener approach, readily accessible reagents, broad substrate scope, high product yields, and operational simplicity.

Original language	English
Pages (from-to)	1789-1794
Number of pages	6
Journal	Journal of Heterocyclic Chemistry
Volume	61
Issue number	11
DOIs	https://doi.org/10.1002/jhet.4902
State	Published - 1 Nov 2024
Externally published	Yes

Keywords

2-arylbenzothiazoles
elemental sulfur
metal-free additive
redox cyclization
three-component reaction

ASJC Scopus subject areas

Organic Chemistry

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10.1002/jhet.4902

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title = "Iodine-Promoted Cascade Redox Cyclization to Access 2-Arylbenzothiazoles Using Elemental Sulfur",

abstract = "A straightforward and efficient method has been developed to access a variety of benzothiazole derivatives via cascade reductive annulation. Iodine mediated, one-pot three-component reaction of o-chloronitroarenes, aryl aldehydes, and elemental sulfur effectively produce benzothiazoles. Moreover, the metal-free strategy allows the facile synthesis of diverse 2-substituted benzothiazoles through multiple carbon–heteroatom bonds in good yields. The present protocol features a greener approach, readily accessible reagents, broad substrate scope, high product yields, and operational simplicity.",

keywords = "2-arylbenzothiazoles, elemental sulfur, metal-free additive, redox cyclization, three-component reaction",

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T1 - Iodine-Promoted Cascade Redox Cyclization to Access 2-Arylbenzothiazoles Using Elemental Sulfur

AU - Chiranjeevi, Yakkanti

AU - Gaware, Sujeet

AU - Chatterjee, Rana

AU - Solanke, Jayshree

AU - Venkateshwarlu, Rapolu

AU - Rao, L. Vaikunta

AU - Simhachalam, Gorle

AU - Dandela, Rambabu

PY - 2024/11/1

Y1 - 2024/11/1

N2 - A straightforward and efficient method has been developed to access a variety of benzothiazole derivatives via cascade reductive annulation. Iodine mediated, one-pot three-component reaction of o-chloronitroarenes, aryl aldehydes, and elemental sulfur effectively produce benzothiazoles. Moreover, the metal-free strategy allows the facile synthesis of diverse 2-substituted benzothiazoles through multiple carbon–heteroatom bonds in good yields. The present protocol features a greener approach, readily accessible reagents, broad substrate scope, high product yields, and operational simplicity.

AB - A straightforward and efficient method has been developed to access a variety of benzothiazole derivatives via cascade reductive annulation. Iodine mediated, one-pot three-component reaction of o-chloronitroarenes, aryl aldehydes, and elemental sulfur effectively produce benzothiazoles. Moreover, the metal-free strategy allows the facile synthesis of diverse 2-substituted benzothiazoles through multiple carbon–heteroatom bonds in good yields. The present protocol features a greener approach, readily accessible reagents, broad substrate scope, high product yields, and operational simplicity.

KW - 2-arylbenzothiazoles

KW - elemental sulfur

KW - metal-free additive

KW - redox cyclization

KW - three-component reaction

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DO - 10.1002/jhet.4902

M3 - Article

AN - SCOPUS:85204430608

SN - 0022-152X

VL - 61

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JO - Journal of Heterocyclic Chemistry

JF - Journal of Heterocyclic Chemistry

IS - 11

ER -

Iodine-Promoted Cascade Redox Cyclization to Access 2-Arylbenzothiazoles Using Elemental Sulfur

Abstract

Keywords

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