Formation of an unexpected 3,3-diphenyl-3H-indazole through a facile intramolecular [2 + 3] cycloaddition of the diazo intermediate

King, AT; Hiscocks, HG; Matesic, L; Bhadbhade, M; Bishop, R; Ung, AT

Formation of an unexpected 3,3-diphenyl-3H-indazole through a facile intramolecular [2 + 3] cycloaddition of the diazo intermediate

King, AT

Hiscocks, HG

Matesic, L

Bhadbhade, M

Bishop, R

Ung, AT

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Publication Type:: Journal Article
Citation:: Beilstein Journal of Organic Chemistry, 2019, 15 pp. 1347 - 1354
Issue Date:: 2019-01-01

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Field	Value	Language
dc.contributor.author	King, AT https://orcid.org/0000-0003-4843-6391	en_US
dc.contributor.author	Hiscocks, HG https://orcid.org/0000-0002-5587-8289	en_US
dc.contributor.author	Matesic, L https://orcid.org/0000-0001-8115-8325	en_US
dc.contributor.author	Bhadbhade, M https://orcid.org/0000-0003-3693-9063	en_US
dc.contributor.author	Bishop, R https://orcid.org/0000-0002-6067-7289	en_US
dc.contributor.author	Ung, AT https://orcid.org/0000-0002-5665-0702	en_US
dc.date.available	2019-06-07	en_US
dc.date.issued	2019-01-01	en_US
dc.identifier.citation	Beilstein Journal of Organic Chemistry, 2019, 15 pp. 1347 - 1354	en_US
dc.identifier.uri	http://hdl.handle.net/10453/135344
dc.description.abstract	© 2019 King et al.; licensee Beilstein-Institut. License and terms: see end of document. The one-pot reaction of 2,6-bis(diphenylmethyl)-4-methoxyaniline with tert-butylnitrite, BTEAC and DABSO in the presence of CuCl2 provided an unexpected 3H-indazole product 8. The structure of the compound was determined by HRMS, IR, NMR and further confirmed by single crystal X-ray crystallography. The compound crystallises in the triclinic P-1 space group, with unit cell parameters a = 9.2107 (4), b = 10.0413 (5), c = 14.4363 (6) Å, α = 78.183 (2), β = 87.625 (2), γ = 71.975 (2)°. The formation of 8 proceeded through a facile intramolecular [2 + 3] cycloaddition of the diazo intermediate 9. The molecules of 8 are organised by edge-face Ar-H···π, face-face π···π, and bifurcated OCH2-H···N interactions. In addition to these, there are Ar-H···H-Ar close contacts, (edge-edge and surrounding inversion centres) arranged as infinite tapes along the a direction.	en_US
dc.relation.ispartof	Beilstein Journal of Organic Chemistry	en_US
dc.relation.isbasedon	10.3762/bjoc.15.134	en_US
dc.subject.classification	Organic Chemistry	en_US
dc.title	Formation of an unexpected 3,3-diphenyl-3H-indazole through a facile intramolecular [2 + 3] cycloaddition of the diazo intermediate	en_US
dc.type	Journal Article
utslib.citation.volume	15	en_US
utslib.for	0305 Organic Chemistry	en_US
pubs.embargo.period	Not known	en_US
pubs.organisational-group	/University of Technology Sydney
pubs.organisational-group	/University of Technology Sydney/Faculty of Science
pubs.organisational-group	/University of Technology Sydney/Faculty of Science/School of Mathematical and Physical Sciences
pubs.organisational-group	/University of Technology Sydney/Strength - CCET - Centre for Clean Energy Technology
utslib.copyright.status	open_access
pubs.publication-status	Published	en_US
pubs.volume	15	en_US

Abstract:

© 2019 King et al.; licensee Beilstein-Institut. License and terms: see end of document. The one-pot reaction of 2,6-bis(diphenylmethyl)-4-methoxyaniline with tert-butylnitrite, BTEAC and DABSO in the presence of CuCl2 provided an unexpected 3H-indazole product 8. The structure of the compound was determined by HRMS, IR, NMR and further confirmed by single crystal X-ray crystallography. The compound crystallises in the triclinic P-1 space group, with unit cell parameters a = 9.2107 (4), b = 10.0413 (5), c = 14.4363 (6) Å, α = 78.183 (2), β = 87.625 (2), γ = 71.975 (2)°. The formation of 8 proceeded through a facile intramolecular [2 + 3] cycloaddition of the diazo intermediate 9. The molecules of 8 are organised by edge-face Ar-H···π, face-face π···π, and bifurcated OCH2-H···N interactions. In addition to these, there are Ar-H···H-Ar close contacts, (edge-edge and surrounding inversion centres) arranged as infinite tapes along the a direction.

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http://hdl.handle.net/10453/135344