Synthesis of 4H-3-aryl-2-cyano-1,4-benzothiazine 1,1-dioxides for antiviral studies

Phillip D. Wilkerson; Andrew C. Bean; Chad E. Stephens

doi:10.1515/hc-2017-0028

Synthesis of 4H-3-aryl-2-cyano-1,4-benzothiazine 1,1-dioxides for antiviral studies

Phillip D. Wilkerson
, Andrew C. Bean
, Chad E. Stephens

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

1 Scopus citations

Abstract

2-Cyano-substituted 1,4-benzothiazine 1,1-dioxides, required for antiviral studies, were prepared by a reductive cyclodehydration of an ortho-nitro sulfone precursor containing a pendant aryl ketone group. The ring-forming reaction also furnishes a non-cyclized benzamide as a major byproduct via an unexpected acyl transfer reaction.

Original language	English (US)
Pages (from-to)	101-103
Number of pages	3
Journal	Heterocyclic Communications
Volume	23
Issue number	2
DOIs	https://doi.org/10.1515/hc-2017-0028
State	Published - Apr 1 2017

Keywords

1,4-benzothiazine
acyl transfer
antiviral sulfone
cyclodehydration
iron reduction

ASJC Scopus subject areas

Organic Chemistry

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10.1515/hc-2017-0028

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title = "Synthesis of 4H-3-aryl-2-cyano-1,4-benzothiazine 1,1-dioxides for antiviral studies",

abstract = "2-Cyano-substituted 1,4-benzothiazine 1,1-dioxides, required for antiviral studies, were prepared by a reductive cyclodehydration of an ortho-nitro sulfone precursor containing a pendant aryl ketone group. The ring-forming reaction also furnishes a non-cyclized benzamide as a major byproduct via an unexpected acyl transfer reaction.",

keywords = "1,4-benzothiazine, acyl transfer, antiviral sulfone, cyclodehydration, iron reduction",

author = "Wilkerson, \{Phillip D.\} and Bean, \{Andrew C.\} and Stephens, \{Chad E.\}",

note = "Publisher Copyright: {\textcopyright} 2017 Walter de Gruyter GmbH, Berlin/Boston 2017.",

year = "2017",

month = apr,

day = "1",

doi = "10.1515/hc-2017-0028",

language = "English (US)",

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journal = "Heterocyclic Communications",

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T1 - Synthesis of 4H-3-aryl-2-cyano-1,4-benzothiazine 1,1-dioxides for antiviral studies

AU - Wilkerson, Phillip D.

AU - Bean, Andrew C.

AU - Stephens, Chad E.

PY - 2017/4/1

Y1 - 2017/4/1

N2 - 2-Cyano-substituted 1,4-benzothiazine 1,1-dioxides, required for antiviral studies, were prepared by a reductive cyclodehydration of an ortho-nitro sulfone precursor containing a pendant aryl ketone group. The ring-forming reaction also furnishes a non-cyclized benzamide as a major byproduct via an unexpected acyl transfer reaction.

AB - 2-Cyano-substituted 1,4-benzothiazine 1,1-dioxides, required for antiviral studies, were prepared by a reductive cyclodehydration of an ortho-nitro sulfone precursor containing a pendant aryl ketone group. The ring-forming reaction also furnishes a non-cyclized benzamide as a major byproduct via an unexpected acyl transfer reaction.

KW - 1,4-benzothiazine

KW - acyl transfer

KW - antiviral sulfone

KW - cyclodehydration

KW - iron reduction

UR - https://www.scopus.com/pages/publications/85017310076

UR - https://www.scopus.com/pages/publications/85017310076#tab=citedBy

U2 - 10.1515/hc-2017-0028

DO - 10.1515/hc-2017-0028

M3 - Article

AN - SCOPUS:85017310076

SN - 0793-0283

VL - 23

SP - 101

EP - 103

JO - Heterocyclic Communications

JF - Heterocyclic Communications

IS - 2

ER -

Synthesis of 4H-3-aryl-2-cyano-1,4-benzothiazine 1,1-dioxides for antiviral studies

Abstract

Keywords

ASJC Scopus subject areas

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