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New Journal of Chemistry
Page 4 of 5
DOI: 10.1039/C8NJ02312C
COMMUNICATION
Journal Name
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To see reviews: (a) G. Cravotto, P. Cintas, Chem. Soc. Rev.,
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with air or water. Although, Ugi IMCR is considered as
multicomponent click reaction due to its significant similar
features with click reaction,22 the mild, green and solvent-free
IMCR involving click [3 + 2] cycloaddition has not yet been
reported. Thus, to the best of our knowledge, this protocol
reported here is first mild, green and solvent-free strategy so
far of an IMCCR to synthesize heterocycles. Moreover, for this
study we used ultrasonic cleaning bath (45 kHz) which is an
excellent alternative non-conventional source of energy, with
very good sound distribution throughout liquid bath and is
inexpensive.
,
7
8
9
M. S. Singh, S. Chowdhury, RSC Adv., 2012,
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1
All synthesized compounds were characterized by H, 13C,
C. A. Seavers, R. L. M. van Montfort, J. Med. Chem., 2006, 49
,
FT-IR and HRMS.
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Ross, U.S. Patent 4,010,179, 1977; (g) W. -W. Dong, J. Zhao,
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In conclusion, we have developed an efficient USI assisted
strategy to improve the synthesis of 1-ST’s via novel IMCCR
approach involving [3 + 2] cycloaddition. To our knowledge,
this is the first protocol for mild and green synthesis of 1-ST’s
via MCR and first IMCR to do so. Also, this is the first solvent
and catalyst-free, mild and green IMCR strategy using water as
a component towards heterocycles. It is worthy to mention
that, this is first solvent and catalyst-free click via [3 + 2]
cycloaddition methodology wherein water generated HN3 is
used. This developed IMCCR strategy has several advantages
over the previously reported MCR strategy such as solvent,
catalyst and column-free synthesis, short reaction times, mild
reaction conditions, high yields, environmental friendliness
and operational simplicity. Besides, this strategy should prove
useful for the facile synthesis of such 1-ST scaffolds on an
industrial scale. It is important to note that present IMCCR
methodology completely meet the click and green chemistry
criteria.
11 E. Oliver-Mandela, B. Alagna, Gazz. Chim. Ital. 1910, 40, 442.
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R.G.-M. thanks CONACYT for financial support CONACYT
CB- 2016-285622 and DAIP-UG 193/2018 projects. S.G.P.
(636753/573230) and M.A.R.-G. (707974/585367) thanks
CONACYT- México for a scholarship and Laboratorio Nacional
de Caracterización de Propiedades Fisicoquímícas y Estructura
Molecular (CONACYT-México, Project: 123732).
19 (a) M. V. Basavanag Unnamatla, A. Islas-Jacome, A. Quezada-
Soto, S. C. Ramírez-López, M. Flores-Álamo, R. Gámez-
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Rojas-Lima, J. O. C. Jiménez-Halla, R. Gámez-Montaño, ACS
Conflicts of interest
There are no conflicts to declare.
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