Catalyst- and Additive-Free Approach to Constructing Benzo-oxazine, Benzo-oxazepine, and Benzo-oxazocine: O Atom Transfer and C═O, C–N, and C–O Bond Formation at Room Temperature

Arnab Ghosh; Rajeev V. Hegde; Haridas B. Rode; Ram Ambre; Manoj Vasisht Mane; Siddappa A. Patil; Balasubramanian Sridhar; Ramesh B. Dateer

doi:10.1021/acs.orglett.1c02895

Catalyst- and Additive-Free Approach to Constructing Benzo-oxazine, Benzo-oxazepine, and Benzo-oxazocine: O Atom Transfer and C═O, C–N, and C–O Bond Formation at Room Temperature

Arnab Ghosh, Rajeev V. Hegde, Haridas B. Rode, Ram Ambre, Manoj Vasisht Mane, Siddappa A. Patil, Balasubramanian Sridhar, Ramesh B. Dateer

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

8 Scopus citations

Abstract

An exclusive synthesis of benzo-oxazine, benzo-oxazepine, and benzo-oxazocine from aryl propanal and 2-(hydroxyamino)phenyl alcohol under metal-free conditions is described. O atom transfer and formation of new C═O, C-N, and C-O bonds occur at room temperature to form six-, seven-, and eight-membered heterocycles under one-pot reaction conditions without using an external oxidant and base. The photophysical properties are studied using ultraviolet-visible absorption and photoluminescence. The mechanistic elucidation is well supported by control experiment and literature precedents.

Original language	English (US)
Journal	Organic Letters
DOIs	https://doi.org/10.1021/acs.orglett.1c02895
State	Published - Oct 13 2021

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Physical and Theoretical Chemistry

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10.1021/acs.orglett.1c02895

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@article{cf296076095a4711b2b855d640ea5742,

title = "Catalyst- and Additive-Free Approach to Constructing Benzo-oxazine, Benzo-oxazepine, and Benzo-oxazocine: O Atom Transfer and C═O, C–N, and C–O Bond Formation at Room Temperature",

abstract = "An exclusive synthesis of benzo-oxazine, benzo-oxazepine, and benzo-oxazocine from aryl propanal and 2-(hydroxyamino)phenyl alcohol under metal-free conditions is described. O atom transfer and formation of new C═O, C-N, and C-O bonds occur at room temperature to form six-, seven-, and eight-membered heterocycles under one-pot reaction conditions without using an external oxidant and base. The photophysical properties are studied using ultraviolet-visible absorption and photoluminescence. The mechanistic elucidation is well supported by control experiment and literature precedents.",

author = "Arnab Ghosh and Hegde, {Rajeev V.} and Rode, {Haridas B.} and Ram Ambre and Mane, {Manoj Vasisht} and Patil, {Siddappa A.} and Balasubramanian Sridhar and Dateer, {Ramesh B.}",

note = "KAUST Repository Item: Exported on 2021-10-21 Acknowledgements: The authors thank DST-SERB, Government of India, for financial support through Research Grants SB/S2/RJN-042/2017 and ECR/2017/002207. This Letter is CSIR-IICT Communication IICT/Pubs./2021/289. The authors are also thankful for a Jain University Start-up Research Grant. The authors thank Dr. Ahipa T. N., Jain University, for valuable input during the study of photophysical properties.",

year = "2021",

month = oct,

day = "13",

doi = "10.1021/acs.orglett.1c02895",

language = "English (US)",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

}

TY - JOUR

T1 - Catalyst- and Additive-Free Approach to Constructing Benzo-oxazine, Benzo-oxazepine, and Benzo-oxazocine: O Atom Transfer and C═O, C–N, and C–O Bond Formation at Room Temperature

AU - Ghosh, Arnab

AU - Hegde, Rajeev V.

AU - Rode, Haridas B.

AU - Ambre, Ram

AU - Mane, Manoj Vasisht

AU - Patil, Siddappa A.

AU - Sridhar, Balasubramanian

AU - Dateer, Ramesh B.

N1 - KAUST Repository Item: Exported on 2021-10-21 Acknowledgements: The authors thank DST-SERB, Government of India, for financial support through Research Grants SB/S2/RJN-042/2017 and ECR/2017/002207. This Letter is CSIR-IICT Communication IICT/Pubs./2021/289. The authors are also thankful for a Jain University Start-up Research Grant. The authors thank Dr. Ahipa T. N., Jain University, for valuable input during the study of photophysical properties.

PY - 2021/10/13

Y1 - 2021/10/13

N2 - An exclusive synthesis of benzo-oxazine, benzo-oxazepine, and benzo-oxazocine from aryl propanal and 2-(hydroxyamino)phenyl alcohol under metal-free conditions is described. O atom transfer and formation of new C═O, C-N, and C-O bonds occur at room temperature to form six-, seven-, and eight-membered heterocycles under one-pot reaction conditions without using an external oxidant and base. The photophysical properties are studied using ultraviolet-visible absorption and photoluminescence. The mechanistic elucidation is well supported by control experiment and literature precedents.

AB - An exclusive synthesis of benzo-oxazine, benzo-oxazepine, and benzo-oxazocine from aryl propanal and 2-(hydroxyamino)phenyl alcohol under metal-free conditions is described. O atom transfer and formation of new C═O, C-N, and C-O bonds occur at room temperature to form six-, seven-, and eight-membered heterocycles under one-pot reaction conditions without using an external oxidant and base. The photophysical properties are studied using ultraviolet-visible absorption and photoluminescence. The mechanistic elucidation is well supported by control experiment and literature precedents.

UR - http://hdl.handle.net/10754/672908

UR - https://pubs.acs.org/doi/10.1021/acs.orglett.1c02895

U2 - 10.1021/acs.orglett.1c02895

DO - 10.1021/acs.orglett.1c02895

M3 - Article

C2 - 34643397

SN - 1523-7060

JO - Organic Letters

JF - Organic Letters

ER -

Catalyst- and Additive-Free Approach to Constructing Benzo-oxazine, Benzo-oxazepine, and Benzo-oxazocine: O Atom Transfer and C═O, C–N, and C–O Bond Formation at Room Temperature

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CCDC 2058417: Experimental Crystal Structure Determination : 2-(1,4-dihydro-2H-3,1-benzoxazin-2-ylidene)-1-phenylethan-1-one

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Catalyst- and Additive-Free Approach to Constructing Benzo-oxazine, Benzo-oxazepine, and Benzo-oxazocine: O Atom Transfer and C═O, C–N, and C–O Bond Formation at Room Temperature

Abstract

ASJC Scopus subject areas

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Datasets

CCDC 2058417: Experimental Crystal Structure Determination : 2-(1,4-dihydro-2H-3,1-benzoxazin-2-ylidene)-1-phenylethan-1-one

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