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Green Chemistry
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ARTICLE
Journal Name
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C.-L. Sun and Z.-J. Shi, Chem. Rev., 2014, 114, 9219–9280.
Conclusions
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ch. 2.
A number of key issues have been addressed in this study. The
remote-site C–H alkenylation of indolizines is feasible under
metal-free conditions. The most impressive peculiarity of this
transmutation is that a single starting material is deployed,
with the new alkenyl substituent bound to the indolizine
nucleus in the product being derived from another molecule of
the starting indolizine and being incorporated through a novel
regio- and stereoselective Csp2–Csp2 bond formation. Given that
the products keep the original structure with the only
substitution of a hydrogen atom, the whole process could be
described as a case of “molecular clone transplantation”. This
type of reaction in which the same compound acts as a
nucleophile and electrophile with the partial grafting of the
latter on the former is infrequent in organic synthesis, albeit
the aldol self-condensation could be a simplistic example.
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P. B. Arockiam and P. H. Dixneuf, Chem. Rev., 2012, 112
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,
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These products are well-defined D-A--A reddish-to-deep
(a) D. Leow, G. Li, T.-S. Mei and J.-Q. Yu, Nature, 2012, 486
,
violet dyes in the solid state which split into two rotamers in
solution. An introductory study to the optical features of these
dyes reveals a particle-size dependent colour, high coloration
power and solvatochromic character, also in plastic materials.
Moreover, the indolizine/chalcone hybrid structures obtained
by this procedure are new and their properties can make
improvements to current applications of indolizine- or
chalcone-based materials or may allow the discovery of new
applications. This survey opens a type of reactivity up to
heterocyclic chemistry which might be extended to other
properly substituted heterocyclic compounds. The facts that
the synthetic procedure is easy (acid-base treatment), mild
(ambient temperature), can be conducted in one pot from
commercial chemicals and it is scalable to multigram scale
pave the way for the future industrial utilisation of these
materials.
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Zhang, K. Tanaka and J.-Q. Yu, Nature, 2017, 543, 538–542.
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Conflicts of interest
12 H. Hu, Y. Liu, H. Zhong, Y. Zhu, C. Wang and M. Ji, Chem.
Asian J., 2012, , 884–888.
There are no conflicts to declare.
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13 (a) H. E. Eastman, C. Jamieson and A. J. B. Watson, Aldrichim.
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Sneddon, R. McElroy, S. Abou-Shehadad and P. J. Dunne,
Green Chem., 2016, 18, 288–296.
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Chem. Soc. Rev., 2013, 42, 6019–6031; (c) A. N. Uglov, A.
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Acknowledgements
This work was generously supported by the Spanish Ministerio
de Economía y Competitividad (MINECO; CTQ2011-24151 and
CTQ-2015-66624-P) and the Generalitat Valenciana (GV; grants
no. APOTIP/2015/014 and AEST/2015/001). M.J.A. and M.J.G.-
S. are grateful to the Instituto de Síntesis Orgánica (ISO) for
both pre-doctoral grants (contracts no. I-PAS-44/13 and I-PAS-
11/16). We would like to acknowledge especially Dr. Diana
Almasi (ISO) for optimizing the large-scale synthesis of the dye
2a as well as IQAP Masterbatch Group S.L. and Colortech
Química S.L. for testing the dyes in different plastic materials.
2013, 42
, 2039–2058; (c) Viewpoint: L. Kloo, Chem.
Commun., 2013, 49, 6580–6583.
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Pharm. Sci. Rev. Res., 2011, 11, 159–163; (b) G. S. Sing and E.
E. Mmatli, Eur. J. Med. Chem., 2011, 46, 5237–5257.
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Notes and references
† Present address (M.J.A.): Sharda Cropchem España S. L.,
Carril Condomina (Atalaya Business Center), 30006 Murcia,
Spain.
This article is dedicated to Prof. Irina P. Beletskaya on the
occasion of her 85th birthday
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, 1913–1927; (d) J. Handzlik, A. Matys and K. Kieć-
10 | J. Name., 2012, 00, 1-3
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