70 Page 8 of 9
J. Chem. Sci. (2018) 130:70
M, Ziania N and Mosset P 2011 Synthesis and character-
ization of 1-formyl-3-phenyl-5-aryl-2-pyrazolines Eur.
J. Chem. 2 311; (d) Nasr-Esfahani M, Daghaghale M
and Taei M 2017 Catalytic synthesis of chalcones and
pyrazolines using nanorod vanadate sulfuric acid: An
efficient and reusable catalyst J. Chin. Chem. Soc. 64 17
2. (a) Gayon E, Szymczyk M, Gerard H, Vrancken E and
Campagne J M 2012 Stereoselective and catalytic access
to β-enaminones: an entry to pyrimidines J. Org. Chem.
77 9205; (b) Palmieri G and Cimarelli C 2006 Chemo-
and stereoselective reduction of enaminones for the
preparation of biologically active compounds ARKIVOC
vi 104
˙
3. (a) Stompor M, Kałuz˙ny
M and Zarowska B
2016 Biotechnological methods for chalcone reduc-
tion using whole cells of Lactobacillus, Rhodococ-
cus and Rhodotorula strains as a way to produce new
derivatives Appl. Microbiol. Biotechnol. 100 8371; (b)
Ritter M, Martins R M, Rosa S A, Malavolta J L, Lund R
G, Flores A F C and Pereira C M P 2015 Green synthe-
sis of chalcones and microbiological evaluation J. Braz.
Chem. Soc. 26 1201; (c) Valdameri G, Gauthier C, Ter-
reux R, Kachadourian R, Day B J, Winnischofer S M
B, Rocha M E M, Frachet V, Ronot X, Pietro A D and
Boumendjel A 2012 Investigation of chalcones as selec-
tive inhibitors of the breast cancer resistance protein:
critical role of methoxylation in both inhibition potency
and cytotoxicity J. Med. Chem. 55 3193
Scheme 2. Probable mechanism via Michael addition.
onto alkynones proceeds without affecting 1◦ amino
groups (aromatic and aliphatic) present in the substrate
and provides a synthetically useful handle in the prod-
ucts for further elaboration. The method involves a
facile route, utilizing simple and easily accessible start-
ing materials under non-toxic environment increases the
synthetic utility of the developed protocol.
4. (a) Lefemine D V, Damn M and Baratschi F 1962
Isolation and characterization mitiromycin and other
antibiotics J. Am. Chem. Soc. 84 3184; (b) Collinus J
F 1965 Application of chalcone in synthesis of 1-(1,
5-benzodiazepino) substituted analogues of indole Brit.
Med. Bull. 21 223; (c) Schach V W M and Els H 1961
Intramolecular cyclization of unsaturated diazoketones
J. Am. Chem. Soc. 83 4678; (d) Garattini S and Valzelli
L 1965 Serotonin (Amsterdam: Elsevier) p. 277
5. (a) Karpov A S and Muller T J J 2003 New entry
to a three-component pyrimidine synthesis by TMS-
ynones via Sonogashira coupling Org. Lett. 5 3451; (b)
Karpov A S and Muller T J J 2003 Straightforward
novel one-pot enaminone and pyrimidine syntheses by
coupling-addition-cyclocondensation sequences Synthe-
sis 18 2815
6. (a) Dixon K and Greenhill J V 1974 A study of the
rates of hydrolysis of certain enaminones J. Chem.
Soc., Perkin Trans. 2 164; (b) Greenhill, J V 1976
Aromatic enaminones. Part 1. Ultraviolet absorption of
N-aryl enaminones derived from dimedone J. Chem.
Soc., Perkin I 2207; (c) Dixon K and Greenhill J V 1976
Use of cyclohexane-1,3-dione derivatives in the prepara-
tion of enaminones J. Chem. Soc., Perkin Trans. I 2211
7. (a) Yang Y, Shen Y, Wang X, Zhang Y, Wang D and
Shi X 2016 Triazole acetyl gold (III) catalyzed Meyer–
Schuster rearrangement of propargyl alcohols Tetrahe-
dron Lett. 57 2280; (b) Gandeepan P, Rajamalli P and
Cheng C H 2014 palladium-catalyzed dehydrogenative
β-arylation of simple saturated carbonyls by aryl halides
ACS Catal. 4 4485; (c) García-Álvarez J, Díez J, Vidal
C and Vicent C 2013 New Ag (I)–Iminophosphorane
coordination polymers as efficient catalysts precursors
for the mw-assisted meyer–schuster rearrangement of
Supplementary Information (SI)
Characterization data and copies of 1H, 13C NMR and HRMS
spectra for selected compounds are reported, which available
Acknowledgements
We gratefully acknowledge the Council of Scientific and
Industrial Research, India [02(0264)/16/EMR-II] for finan-
cial support and USIC, University of Delhi for providing
instrumentation facilities. M.P. and Sushmita are thankful to
DST-SERB and UGC, New Delhi for fellowships.
References
1. (a) Jioui I, Danoun K, Solhy A, Jouiad M, Zahouily
M, Essaid B, Len C and Fihri A 2016 Modified fluo-
rapatite as a highly efficient catalyst for the synthesis
of chalcones via Claisen–Schmidt condensation reac-
tion J. Indus. Eng. Chem. 39 218; (b) Li Z, Zhao H,
Han H, Liu Y, Song J, Guo W, Chu W and Sun Z
2017 Graphene-supported ZnO nanoparticles: An effi-
cient heterogeneous catalyst for the Claisen-Schmidt
condensation reaction without additional base Tetrahe-
dron Lett. 58 3984; (c) Sida A, Lamaraa K, Mokhtaria