One-pot multistep synthesis of bipolar carbazolo-phenazines: Hydrogen bond control of Diels-Alder cycloaddition and application for fluoride sensing

Abhaya Kumar Mishra; Arindam Mukhopadhyay; Jarugu Narasimha Moorthy

doi:10.1016/j.tet.2017.02.052

One-pot multistep synthesis of bipolar carbazolo-phenazines: Hydrogen bond control of Diels-Alder cycloaddition and application for fluoride sensing

Abhaya Kumar Mishra
, Arindam Mukhopadhyay
, Jarugu Narasimha Moorthy

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

15 Scopus citations

Abstract

Access to novel bipolar carbazolo-phenazines is demonstrated by one-pot IBX-initiated multistep cascade, which involves oxidation of 2-naphthols to 1,2-naphthoquinones, Diels-Alder cycloaddition, aerial dehydroaromatization and cyclocondensation. With unprotected dienic indolylacrylates, N[sbnd]H⋯O hydrogen bonding in the transition state controls the product selectivity almost exclusively in favor of Diels-Alder cycloaddition over the competing Michael addition. The utility of one of the carbazolo-phenzines as applied to selective naked-eye sensing of fluoride is demonstrated.

Original language	English
Pages (from-to)	2210-2216
Number of pages	7
Journal	Tetrahedron
Volume	73
Issue number	16
DOIs	https://doi.org/10.1016/j.tet.2017.02.052
State	Published - 2017
Externally published	Yes

Keywords

Cycloaddition
Cyclocondensation
Dehydroaromatization
Naphthoquinone
Phenazines

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10.1016/j.tet.2017.02.052

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title = "One-pot multistep synthesis of bipolar carbazolo-phenazines: Hydrogen bond control of Diels-Alder cycloaddition and application for fluoride sensing",

abstract = "Access to novel bipolar carbazolo-phenazines is demonstrated by one-pot IBX-initiated multistep cascade, which involves oxidation of 2-naphthols to 1,2-naphthoquinones, Diels-Alder cycloaddition, aerial dehydroaromatization and cyclocondensation. With unprotected dienic indolylacrylates, N[sbnd]H⋯O hydrogen bonding in the transition state controls the product selectivity almost exclusively in favor of Diels-Alder cycloaddition over the competing Michael addition. The utility of one of the carbazolo-phenzines as applied to selective naked-eye sensing of fluoride is demonstrated.",

keywords = "Cycloaddition, Cyclocondensation, Dehydroaromatization, Naphthoquinone, Phenazines",

author = "Mishra, \{Abhaya Kumar\} and Arindam Mukhopadhyay and Moorthy, \{Jarugu Narasimha\}",

note = "Funding Information: JNM is thankful to the Science and Engineering Research Board (SERB) (SB/S2/JCB-52/2014), New Delhi, for financial support through J. C. Bose fellowship. AKM and AM gratefully acknowledge the University Grants Commission (UGC) and Council of Scientific and Industrial Research (CSIR), New Delhi, respectively, for senior research fellowships. Publisher Copyright: {\textcopyright} 2017 Elsevier Ltd",

year = "2017",

doi = "10.1016/j.tet.2017.02.052",

language = "English",

volume = "73",

pages = "2210--2216",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "16",

}

TY - JOUR

T1 - One-pot multistep synthesis of bipolar carbazolo-phenazines

T2 - Hydrogen bond control of Diels-Alder cycloaddition and application for fluoride sensing

AU - Mishra, Abhaya Kumar

AU - Mukhopadhyay, Arindam

AU - Moorthy, Jarugu Narasimha

N1 - Funding Information: JNM is thankful to the Science and Engineering Research Board (SERB) (SB/S2/JCB-52/2014), New Delhi, for financial support through J. C. Bose fellowship. AKM and AM gratefully acknowledge the University Grants Commission (UGC) and Council of Scientific and Industrial Research (CSIR), New Delhi, respectively, for senior research fellowships. Publisher Copyright: © 2017 Elsevier Ltd

PY - 2017

Y1 - 2017

N2 - Access to novel bipolar carbazolo-phenazines is demonstrated by one-pot IBX-initiated multistep cascade, which involves oxidation of 2-naphthols to 1,2-naphthoquinones, Diels-Alder cycloaddition, aerial dehydroaromatization and cyclocondensation. With unprotected dienic indolylacrylates, N[sbnd]H⋯O hydrogen bonding in the transition state controls the product selectivity almost exclusively in favor of Diels-Alder cycloaddition over the competing Michael addition. The utility of one of the carbazolo-phenzines as applied to selective naked-eye sensing of fluoride is demonstrated.

AB - Access to novel bipolar carbazolo-phenazines is demonstrated by one-pot IBX-initiated multistep cascade, which involves oxidation of 2-naphthols to 1,2-naphthoquinones, Diels-Alder cycloaddition, aerial dehydroaromatization and cyclocondensation. With unprotected dienic indolylacrylates, N[sbnd]H⋯O hydrogen bonding in the transition state controls the product selectivity almost exclusively in favor of Diels-Alder cycloaddition over the competing Michael addition. The utility of one of the carbazolo-phenzines as applied to selective naked-eye sensing of fluoride is demonstrated.

KW - Cycloaddition

KW - Cyclocondensation

KW - Dehydroaromatization

KW - Naphthoquinone

KW - Phenazines

UR - https://www.scopus.com/pages/publications/85014750034

U2 - 10.1016/j.tet.2017.02.052

DO - 10.1016/j.tet.2017.02.052

M3 - Article

AN - SCOPUS:85014750034

SN - 0040-4020

VL - 73

SP - 2210

EP - 2216

JO - Tetrahedron

JF - Tetrahedron

IS - 16

ER -

One-pot multistep synthesis of bipolar carbazolo-phenazines: Hydrogen bond control of Diels-Alder cycloaddition and application for fluoride sensing

Abstract

Keywords

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