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CC BY-ND-NC 4.0 · SynOpen 2018; 02(02): 0150-0160
DOI: 10.1055/s-0036-1591960
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Synthesis of Substituted Pyrido-oxazine through Tandem SN2 and SNAr Reaction

Mosim Amin Pathan
Department of Chemistry, Indian Institute of Technology Hyderabad, Kandi, Sangareddy, Telangana, 502 285, India   Email: faiz@iith.ac.in
,
Faiz Ahmed Khan*
Department of Chemistry, Indian Institute of Technology Hyderabad, Kandi, Sangareddy, Telangana, 502 285, India   Email: faiz@iith.ac.in
› Author AffiliationsF.A.K. gratefully acknowledges DBT for financial support. M.A.P. thanks CSIR for the award of a fellowship
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Publication History

Received: 15 January 2018

Accepted: 23 February 2018

Publication Date:
16 May 2018 (online)

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Abstract

Pyrido-oxazine derivatives have been synthesized by employing tandem SN2 and SNAr reaction between 2,4,6-tribromo-3-(2-bromoethoxy)pyridine or 2,4,6-tribromo-3-(3-bromopropoxy)pyridine and a variety of primary amines. Moderate to good regioselectivity in favor of cyclization at the 2-position is observed. Pyrido-oxazine products thus generated are converted into biarylated pyrido-oxazine and terpyridine ligands.

Key words

pyridine - terpyridine - pyrido-oxazines - Suzuki coupling - Stille coupling

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591960.
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