Efficient Syntheses of Diverse N-Heterocycles: The Molybdenum(VI)-Catalyzed Reductive Cyclization of Nitroarenes using Pinacol as a Deoxygenating­ Agent

Abstract Molybdenum(VI)-catalyzed domino reductive cyclization of nitroarenes has been devised for the syntheses of 1,4-benzoxazines and 1,4-benzothiazines in the presence of pinacol as deoxygenating agent. The scope of the described method was further extended to the syntheses of the rarely explore...

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Main Authors: Raghuram Gujjarappa, Nagaraju Vodnala, Arup K. Kabi, Dhananjaya Kaldhi, Mohan Kumar, Uwe Beifuss, Chandi C. Malakar
Format: Article
Language:English
Published: Georg Thieme Verlag KG 2018-04-01
Series:SynOpen
Subjects:
Online Access:http://www.thieme-connect.de/DOI/DOI?10.1055/s-0036-1591572
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author Raghuram Gujjarappa
Nagaraju Vodnala
Arup K. Kabi
Dhananjaya Kaldhi
Mohan Kumar
Uwe Beifuss
Chandi C. Malakar
author_facet Raghuram Gujjarappa
Nagaraju Vodnala
Arup K. Kabi
Dhananjaya Kaldhi
Mohan Kumar
Uwe Beifuss
Chandi C. Malakar
author_sort Raghuram Gujjarappa
collection DOAJ
description Abstract Molybdenum(VI)-catalyzed domino reductive cyclization of nitroarenes has been devised for the syntheses of 1,4-benzoxazines and 1,4-benzothiazines in the presence of pinacol as deoxygenating agent. The scope of the described method was further extended to the syntheses of the rarely explored scaffolds, 1-hydroxyphenazines and quinoxalines. The present method avoids the use of hazardous deoxygenating agents and operates under solvent-free conditions.
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spelling doaj.art-623d494ec0874b729300e8f7b25f70d22022-12-22T01:25:27ZengGeorg Thieme Verlag KGSynOpen2509-93962018-04-0102020138014410.1055/s-0036-1591572Efficient Syntheses of Diverse N-Heterocycles: The Molybdenum(VI)-Catalyzed Reductive Cyclization of Nitroarenes using Pinacol as a Deoxygenating­ AgentRaghuram Gujjarappa0Nagaraju Vodnala1Arup K. Kabi2Dhananjaya Kaldhi3Mohan Kumar4Uwe Beifuss5Chandi C. Malakar6Department of Chemistry, National Institute of Technology ManipurDepartment of Chemistry, National Institute of Technology ManipurDepartment of Chemistry, National Institute of Technology ManipurDepartment of Chemistry, National Institute of Technology ManipurDepartment of Chemistry, National Institute of Technology ManipurInstitut für Chemie, Universität HohenheimDepartment of Chemistry, National Institute of Technology ManipurAbstract Molybdenum(VI)-catalyzed domino reductive cyclization of nitroarenes has been devised for the syntheses of 1,4-benzoxazines and 1,4-benzothiazines in the presence of pinacol as deoxygenating agent. The scope of the described method was further extended to the syntheses of the rarely explored scaffolds, 1-hydroxyphenazines and quinoxalines. The present method avoids the use of hazardous deoxygenating agents and operates under solvent-free conditions.http://www.thieme-connect.de/DOI/DOI?10.1055/s-0036-1591572n-heterocyclesdomino reactionreductive cyclizationnitro­arenesdioxo-mo(vi) complexpinacol
spellingShingle Raghuram Gujjarappa
Nagaraju Vodnala
Arup K. Kabi
Dhananjaya Kaldhi
Mohan Kumar
Uwe Beifuss
Chandi C. Malakar
Efficient Syntheses of Diverse N-Heterocycles: The Molybdenum(VI)-Catalyzed Reductive Cyclization of Nitroarenes using Pinacol as a Deoxygenating­ Agent
SynOpen
n-heterocycles
domino reaction
reductive cyclization
nitro­arenes
dioxo-mo(vi) complex
pinacol
title Efficient Syntheses of Diverse N-Heterocycles: The Molybdenum(VI)-Catalyzed Reductive Cyclization of Nitroarenes using Pinacol as a Deoxygenating­ Agent
title_full Efficient Syntheses of Diverse N-Heterocycles: The Molybdenum(VI)-Catalyzed Reductive Cyclization of Nitroarenes using Pinacol as a Deoxygenating­ Agent
title_fullStr Efficient Syntheses of Diverse N-Heterocycles: The Molybdenum(VI)-Catalyzed Reductive Cyclization of Nitroarenes using Pinacol as a Deoxygenating­ Agent
title_full_unstemmed Efficient Syntheses of Diverse N-Heterocycles: The Molybdenum(VI)-Catalyzed Reductive Cyclization of Nitroarenes using Pinacol as a Deoxygenating­ Agent
title_short Efficient Syntheses of Diverse N-Heterocycles: The Molybdenum(VI)-Catalyzed Reductive Cyclization of Nitroarenes using Pinacol as a Deoxygenating­ Agent
title_sort efficient syntheses of diverse n heterocycles the molybdenum vi catalyzed reductive cyclization of nitroarenes using pinacol as a deoxygenating agent
topic n-heterocycles
domino reaction
reductive cyclization
nitro­arenes
dioxo-mo(vi) complex
pinacol
url http://www.thieme-connect.de/DOI/DOI?10.1055/s-0036-1591572
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