Communications
ChemistrySelect doi.org/10.1002/slct.202000810
z Organic & Supramolecular Chemistry
K2CO3-Promoted Ring-Opening/Cyclization Reactions of
Multi-substituted Donor-Acceptor Cyclopropanes with
Thiourea: Access to 2-Amino-4,6-diarylnicotinonitrile
Derivatives
Shan Wang+,[a] Zengyang Xie+,[b] Mingshuang Li,[a] and Cunde Wang*[a]
The ring-opening/cyclization reactions of substituted 2-acyl-3-
arylcyclopropane-1,1-dicarbonitriles with thiourea promoted by
K2CO3 were investigated successfully. Using the reaction, the
desired 2-amino-4,6-diarylnicotinonitrile derivatives were ob-
tained in good to excellent yields. This work provides a new
strategy for the synthesis of 2-amino-4,6-diarylnicotinonitrile
derivatives.
Donor-acceptor cyclopropanes (D–A cyclopropanes) were re-
cently drawn tremendous amount of attentions,[1] as easily
available building blocks, which have been widely used in
organic synthesis and methodology via 1,3-zwitterionic form,
owing to the ring C C bonds of cyclopropane are promoted by
their high strain energy and by the polarized bond between
the carbon atoms bearing the donor and the acceptor
substituents. Therefore, various transformations including ring-
opening[2] rearrangement,[3] cycloaddition reactions[1,4] were
further investigated. Among D A cyclopropanes, multifunc-
tional D A cyclopropanes such as 2-acyl-3-aryl-1-cyanocyclo-
propane-1-carboxylates and 2-acyl-3-arylcyclopropane-1,1-di-
carbo-nitriles were widely investigated recently, which were
prepared easily by general methods.[5] Multifunctional D A
cyclopropanes easily afforded multifarious 1,3-dipoles in combi-
nation with carbonyl, ester or cyano group via regioselective
C C bond cleavages under the influence of a variety of
conditions for the synthesis of products with increased
structural diversity and complexity.[6] Our idea was to use the
base-promoted cleavage of multifunctional D A cyclopropanes
with two cyano groups at C1 position to generate 1,3-dipoles
in situ, which are then employed in a cyclization reaction with
thiourea for the preparation of heterocycles.
[a] S. Wang,+ M. Li, Prof. C. Wang
School of Chemistry and Chemical Engineering, Yangzhou University, 180
Siwangting Street, Yangzhou 225002, P. R. China Tel: + 86-514-8797-5568
Fax: + 86-514-8797-5244
E-mail: wangcd@yzu.edu.cn
[b] Dr. Z. Xie+
College of Basic Medicine, Jining Medical University, Jining 272067, PR
China
[+] These authors contributed equally to this work and should be considered co-
first authors.
Supporting information for this article is available on the WWW under
https://doi.org/10.1002/slct.202000810
ChemistrySelect 2020, 5, 6011 – 6015
2-Aminonicotinonitrile (2-amino-3-cyanopyridine) is a spe-
cial structural moiety present in many biologically active
molecules. Its derivatives were used as antitumor,[7] carbonic
anhydrase inhibitor,[8] antimicrobial,[9] IKK-β-inhibitors,[10] A2A
adenosine receptor antagonists,[11] antihypertensive,[12] HIV-1
integrase inhibitors,[13] antifungal,[14] antiviral, antibacterial,[15]
and anti-inflammatory agents.[16] Because of inherent biological
activity of 2-aminonicotinonitrile derivatives, the construction
of 2-aminonicotinonitrile motif have been drawn numerous
attentions throughout the years. A number of methods[7a,17] for
the synthesis of substituted 2-aminonicotinonitriles have been
explored, including the mutli-component reactions,[18] the
annulation of oxime ester, malononitrile and aldehydes,[19] the
microwave-assisted cyclization of enaminonitriles and primary
amines.[20] Although great achievements to construct 2-amino-
nicotinonitriles have been made through the multiple-steps
reaction or one-pot mutli-component reactions, developing an
alternative method to synthesize 2-aminonicotinonitriles and
their derivatives is still highly desirable.
The reported investigations showed that mutli-substituted
D–A cyclopropanes can undergo the various transformations
via the C C bond cleavage of ring and these adhered groups.
Recently, the sulfur-containing substrates were paid close
attention to react with D–A cyclopropanes. For examples, the
normal (3 + 2) cycloaddition of thioketones and D–A cyclo-
propanes was investigated for the preparation of 2-substituted
tetrahydrothiophenes.[4b] Soon afterwards, the similar tetrahy-
drothiophenes also were yielded via Fe(OTf)3-promoted (3 + 2)
cycloaddition of D–A cyclopropanes with thionoesters.[4c] Thio-
chalcones as sulfur-containing four-atom building blocks were
reacted in a Lewis acid catalyzed (4 + 3)-cycloaddition reaction
with D–A cyclopropanes for the synthesis of
tetrahydrothiepines.[4d] Previously, thiourea as a common nitro-
gen and sulfur sources has rarely been employed to react with
D–A cyclopropanes. Our group has demonstrated a simple and
efficient strategy to form 2-aminothiophene-3-carboxylates by
a DBU-mediated (4 + 1) annulations of D A cyclopropanes (1-
cyanocyclopropane-1-carboxylates) with thiourea (Scheme 1),[6g]
while Guo and co-workers recently contributed the Yb(OTf)3-
catalyzed (3 + 2) cycloaddition of thiourea with D–A cyclo-
propanes (2-arylcyclopropane-1,1-dicarboxylates) to generate
2-amino-4,5-dihydrothiophene.[21] To continue further exploring
the property of D A cyclopropanes, herein, we demonstrate
that cyclopropane-1,1-dicarbonitriles as a special D A cyclo-
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ChemistrySelect doi.org/10.1002/slct.202000810

Table 1. Optimization of the Reaction Conditions for the Synthesis of 3aa

Entry Base (eq.) Solvent T (°C) t (h) Yield (%)b

1 DBU(1.0) DMF 110 8 33

2 DABCO(1.0) DMF 110 12 trace
3 K2CO3(1.0) DMF 110 10 82
4 Cs2CO3(1.0) DMF 110 12 35
5 Et3N(1.0) DMF 110 12 trace
6 K2CO3(1.0) DMSO 110 10 0
7 K2CO3(1.0) CH3CN reflux 12 trace
8 K2CO3(1.0) EtOH reflux 12 trace
9 K2CO3(1.0) Toluene reflux 12 trace
10 K2CO3(0.5) DMF 110 14 67
11 K2CO3 (2.0) DMF 110 6 78
12 K2CO3(1.0) DMF 80 12 79
Scheme 1. Reported ring-opening/cyclization reactions of D–A cyclopro- 13 K2CO3(1.0) DMF 140 6 65
panes with thiourea and our work. 14c K2CO3(1.0) DMF 110 10 80
a
Reaction conditions: 1 a/2 (76 mg, 1.0 mmol) = 1/1(mol), and base in
solvent (15 mL). bIsolated yields. c1a/2 = 1/2(mol),.
propane with two cyano groups at the C1 position of
cyclopropane react with thiourea in the presence of K2CO3 to
give substituted 2-aminonicotinonitriles (Scheme 1). To the
best of our knowledge, the synthesis of substituted 2-amino- resulted in the product 3 a in 67% yield, albeit requiring a
nicotinonitriles employing D A cyclopropanes is not published. reaction time of 14 h (Table 1, entry 10). Increasing the K2CO3
On the basis of our previous work on organic base- loading to 2.0 equiv. did not have a significant improvement
mediated ring-opening/cyclization reactions of D A cyclo- under otherwise identical conditions (Table 1, entry 11). Addi-
propane compounds, DBU can efficiently promote the (4 + 1) tionally, a slightly lower yield of 3 a was obtained when the
annulations of 1-cyanocyclopropane-1-carboxylates with car- reaction was carried out at 80 °C, but the yield of 3 a evidently
bon disulfide or thiourea to synthesize fully substituted 2- descended at 140 °C, because the high reaction temperature
aminothiophene-3-carboxylates.[6g] The reaction of cyclopro- resulted in the unselective disconnection of D A cyclopropane
pane-1,1-dicarbonitrile 1 a and thiourea (2) was chosen as the (Table 1, entries 12–13). Increasing the thiourea amount to 2.0
model reaction (Table 1). equiv. did not have a significant improvement under otherwise
The reaction was carried out firstly by stirring the mixture identical conditions (Table 1, entry 14). A series of experiments
of cyclopropane-1,1-dicarbonitrile 1 a and thiourea (2) using revealed that the optimal conditions were obtained, the
DBU as a promoter in DMF at 110 °C for 8 h, to the delight of reaction of cyclopropane-1,1-dicarbonitrile 1 a and thiourea (2)
us, the product 3 a was obtained in yield of 33% (Table 1, in the presence of K2CO3 (1.0 equiv) was carried out in DMF for
entry 1). To further improve the reaction, the effects of various 10 h at 110 °C, whereby the yield of product 3 a reached 82%
bases, including DABCO, K2CO3, Cs2CO3, and Et3N were explored (Table 1, entry 3).
under similar reaction conditions (Table 1, entries 2–5). It seems With the optimized reaction conditions in hand, a number
that common organic amines DABCO and Et3N were not of substituted cyclopropane-1,1-dicarbonitriles 1 a-1 p were
beneficial to the reaction, only trace annulation product was examined under the similar conditions and the results are
observed. However, with the use of K2CO3 and Cs2CO3 as the summarized in Table 2. The electron-withdrawing substitutions
promoter, the reaction worked at 110 °C for 10 or 12 h to give (Cl and Br) on 2-aryl and 3-aroyl moieties of cyclopropane-1,1-
the product 3 a in 82% and 35% yield (entries 3–4), respectively. dicarbonitriles provided good yields (Table 2, entries 7–12). In
Considering the replacement of DMF by different solvents for contrast, the electron-donating substitution such as Me had a
the improvement of the reaction, the solvents DMSO, CH3CN, slight impact on the yield (Table 2, entries 1–2, 6, 16). We next
EtOH or toluene were used in the reaction at different reaction explored the influence of ester vs cyano substitution of
temperatures (Table 1, entries 6–9). The results showed that the cyclopropane on pyridine formation using the title reaction
product 3 a was not obtained in DMSO (Table 1, entry 6). With conditions, for example, 1-cyanocyclopropane-1-carboxylate 4
the use of CH3CN, EtOH or toluene as solvent, the reaction was selected as a starting material (Scheme 2). However, the
worked under reflux to give only trace product 3 a (Table 1, desired pyridine derivative was not obtained, the reaction
entries 7–9). The results indicated the important role of the afforded our previously reported 2-aminothiophene-3-carbox-
solvent, DMF was propitious to the formation of the annulation ylate product.[6g] The result implied that the substitution such
product 3 a. Lowering the amount of K2CO3 to 0.5 equiv. still

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Communications
ChemistrySelect doi.org/10.1002/slct.202000810

Table 2. Synthesis of 2-amino-4,6-diarylnicotinonitrile derivatives 3 a-pa

Entry R1 R2 t (h) product Yield(%)b

1 o-Cl p-CH3 10 3a 82
2 o-CH3 H 10 3b 83
3 o-Cl H 9 3c 85
4 m-Br H 8.5 3d 81
5 p-CH3 H 10 3e 85
6 H H 9 3f 76 Figure 1. Molecular structure of 2-amino-4,6-diarylnicotinonitrile 3 d, non-
7 o-Cl p-Cl 11 3g 93 hydrogen atoms are shown at the 30% probability level.
8 p-Br p-Cl 10 3h 95
9 p-Cl p-Cl 11.5 3i 89
10 o-Cl p-Br 10.5 3j 87
11 p-Cl p-Br 10 3k 85
12 o-Br p-Br 12 3l 89 possess an amine and a cyano contiguous substituents at C(2)
13 m-Cl p-Br 10 3m 81 and C(3), two aryl substituents at C(4) and C(6) of pyridine core.
14 o-Cl m-Br 10.5 3n 86
Our previous studies showed that potassium carbonate can
15 m-Cl m-Cl 10 3o 84
16 H m-CH3 8.5 3p 84 selectively promote the disconnection of D A cyclopropane,
a
which is evidently different from the common organic bases.[6a]
reaction condition: substituted cyclopropane-1,1-dicarbonitriles
(1.0 mmol), thiourea (76 mg, 1.0 mmol), K2CO3 (138 mg, 1.0 mmol), DMF
On the basis of the above-described results, we propose the
(15 mL), 110 °C; bisolated yields. mechanism outlined in Scheme 3.
A possible reaction mechanism through selective discon-
nection of cyclopropane ring is proposed. First, potassium
carbonate-mediated ring-opening reaction of 2-acyl-3-arylcy-
clopropane-1,1-dicarbonitrile affords dicyanomethanide with
chalcone unit [A], which undergoes nucleophilic addition to
carbonyl group of [A] chalcone unit to form the intermediate
but-2-en-1-ylidenethiourea [B]. Then, charge-separated reso-
nance structures do contribute very much to the resonance
Scheme 2. Reaction of 1-cyanocyclopropane-1-carboxylate 4 under the
hybrid of 4-(carbamothioylimino)-1,1-dicyano-2,4-diphenylbut-
optimized reaction conditions. 2-en-1-ide [B] to produce an anion [C]. Subsequently, the
intramolecular nucleophilic addition of intermediate [C] to
cyano group and protonation by originating from water forms
the intermediate 2-iminopyridine-1(2H)-carbothioamide [D],
as ester or cyano group of cyclopropane ring plays a key role in following the intermediate [D] transfers easily to the intermedi-
the disconnection of ring.
Subsequently, other compounds containing nitrogen as
nitrogen sources such as ammonium acetate, aniline, benzyl-
amine, n-pentanamine or ethyl glycinate were used in the
reaction of substituted cyclopropane-1,1-dicarbonitrile (1 a) for
the preparation of the desired pyridine derivatives. The results
showed that ammonium acetate, aniline, and n-pentanamine
did not give the desired product (3 a), a trace of the desired
product was obtained using benzylamine. However, when ethyl
glycinate was used as nitrogen sources, the product 3 a was
acquired in the slightly lower yield (47%). Obviously, in the
presence of K2CO3, thiourea (2) is the best nitrogen source for
the above reaction.
Final confirmation for the formation of the reaction
products was obtained by X-ray crystal structure analysis of 2-
amino-4,6-diarylnicotinonitrile 3 d. The structure of 2-amino-
4,6-diarylnicotinonitrile 3 d was unambiguously solved by X-ray
crystallography (Figure 1).[22] X-ray crystallographic analysis Scheme 3. Possible mechanism of the ring-opening/cyclization reactions of
determined that product 2-amino-4,6-diarylnicotinonitrile 3 d substituted D A cyclopropanes with thiourea

ChemistrySelect 2020, 5, 6011 – 6015 6013 © 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Communications
ChemistrySelect doi.org/10.1002/slct.202000810
ate 2-amino-1-carbamothioylpyridin-1-ium [E]. In the presence
of K2CO3, a thiocarbonyl group of intermediate [E] was attacked
by water via nucleophilic addition to afford the intermediate
[F]. The 2-amino-4,6-diarylnicotinonitriles 3 a-p were finally
obtained through removal of carbamothioic S-acid in the
presence of base K2CO3.
In summary, the ring-opening/cyclization reactions of
substituted 2-acyl-3-arylcyclopropane-1,1-dicarbonitriles with
thiourea promoted by K2CO3 were investigated successfully.
This reaction involves a highly efficient multiple domino
sequence consisting of ring opening of substituted 2-acyl-3-
arylcyclopropane-1,1-dicarbonitriles, regioselective condensat-
ion, intramolecular nucleophilic addition and tautomerism as
key steps. Using the reaction, 2-amino-4,6-diarylnicotinonitriles
were obtained in good to excellent yields. This work provides a
new strategy for the synthesis of 2-amino-4,6-diarylnicotinoni-
trile derivatives.
Supporting Information Summary
Supporting information includes experimental details, crystallo-
graphic data for 2-amino-4,6-diarylnicotinonitrile 3 d, character-
ization data for all compounds, including NMR spectra (1H and
13
C NMR) of the compounds are available.
Acknowledgements
This work was financially supported by the Priority Academic
Program Development of Jiangsu Higher Education Institutions .
Support for this work also was provided by the Analysis and Test
Center of Yangzhou University.
Conflict of Interest
The authors declare no conflict of interest.
Keywords: Donor-acceptor cyclopropane (D–A cyclopropane) ·
cyclization reaction · cyclopropane-1,1-dicarbonitrile · thiourea ·
2-aminonicotinonitrile
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