-Thiocyanation of Carbonyl Compounds: A Review

Rajesh H. Vekariya1, Hitesh D. Patel1

1

Department of Chemistry, School of Sciences, Gujarat University, Ahmedabad, India

Corresponding author Hitesh D. Patel E-mail: drhiteshpatel1@gmail.com

Abstract
The -thiocyanation of carbonyl compounds is one of the most important processes in
synthetic organic chemistry. These compounds are important precursors for the
production of various biologically important heterocyclic compounds and other
industrially important products. Ammonium thiocyanate (NH4SCN) is a key reagent for
the production of such class of thiocyanate intermediates. In addition to the inherent
efficiency issues, there are also environmental concerns that need to be addressed.
Therefore, in recent years considerable advances have been made for the synthesis of thiocyanation of carbonyl compounds with high selectivity and yield. In this review, we
have summarized various methods for the synthesis of -thiocyanation carbonyl
compounds.

Graphical Abstract

KEYWORDS: -Thiocyanation, Carbonyl compounds, Ammonium thiocyanate

(NH4SCN)

INTRODUCTION
Thiocyanates have gained considerable importance in various areas of organosulfur
chemistry.[1] Thiocyanate is a versatile synthon which can be readily transformed into
other functional groups such as sulfide,[2] aryl nitrile,[3] thiocarbamate,[4] and thionitrile.[5]
The electrophilic thiocyanation of aromatic, hetero aromatic and ketone compounds is a
direct way for carbon sulfur bond formation and is a very useful reaction in organic
synthesis.[6] The thiocyanate function is an interesting part of the molecule, which will be
readily transformed into the other sulfur-bearing functionalities, especially for producing
compounds with pharmaceutical properties.[7] In addition, thiocyanato functionality can
be used as a masked mercapto group or as a precursor for sulfur-containing heterocyclic
compounds, such as thiazolidine and cyclic thioureas.[810]

In particular, the direct -thiocyanation of ketones is an important carbon-heteroatom

bond forming reaction in organic synthesis. In addition, -thiocyanato carbonyl
compounds are valuable precursors for synthesis of heterocyclic ring systems such as 2amino-1,3-thiazines, thiazoles and their derivatives.[11] Some of these thiazoles exhibit
herbicidal and other important biological activities.[12] In addition, thiocynato group plays
an important function in certain anticancer natural products formed by deglycosylation of
glucosinolates derived from cruciferous vegetables.[13,14] Thus, the direct -thiocyanation
of ketones is of crucial importance.

Generally, -thiocyanato carbonyl compounds are prepared from -halocarbonyl

compounds[15] or -tosyloxycarbonyls[16] or -diazoketones[17] and also by oxidative
thiocyanation of enol ethers.[1820] However, the yields are typically low as a result of the
poor nucleophilicity of the SCN anion. Thus, the development of new and direct
synthetic methods for introducing thiocyanate functionality is always demanded.
Although over a century has passed, no review articles have been published on synthetic
protocols of -thiocyanato carbonyl compounds. Thus, in the present review, we have
discussed various methodologies for synthesis of -thiocyanato carbonyl compounds.

VARIOUS METHODS FOR SYNTHESIS OF -THIOCYANATION OF

CARBONYL COMPOUNDS
Yadav and co-workers have described a selective, mild and an efficient synthetic
methodology for -thiocyanation of ketones possessing -hydrogens, by using
ammonium thiocyanate (NH4SCN) and molecular iodine (I2) in refluxing methanol to
produce the corresponding -ketothiocyanates in excellent yields (Scheme 1a-e).[21] The
use of iodine makes this procedure simple, convenient and cost effective. Various
substituted and sterically hindered acetophenones were undergoes efficiently with this
protocol to afford the corresponding -thiocyanatoketones in high yields. In addition,
cyclic ketones such as 1-tetralone, 2-phenylchroman-4-one, cyclopentanone, 2methylcyclohexanone, 4,4-dimethylcyclohex-2-enone, cycloheptanone, and
cyclododecanone reacted well under similar conditions. Moreover, chroman-2,4-dione
also afforded the corresponding 3-thiocyanato-chroman-2,4-dione in good yield. It was
interesting to note that -thiocyanation of cyclic ketones gave higher yields compared to

acyclic ketones. At room temperature and in the absence of catalyst, reaction does not
proceeded efficiently. While the best results were obtained in reflux condition in the
presence of methanol. To optimize the reaction condition, the authors have tested various
oxidants such as Mn(OAc)3.2H2O, Bi(NO3)3.5H2O and IBX, and I2. Only, I2 was found to
be the most effective in terms of conversion and reaction rates. The authors have also
described the proposed reaction mechanism, and according to them the reaction most
likely proceed via the formation of active thiocyanogen, (SCN)2 from I2 and NH4SCN. In
second step the produced (SCN)2 reacts rapidly with the enolizable ketone to produce ketothiocyanate.

A convenient approach for the direct -thiocyanation of carbonyl and -dicarbonyl

compounds in high to excellent yield have been investigated by Kumar and co-workers
by employing ammonium thiocyanate as the thiocyanating agent and potassium
peroxydisulfate (K2S2O8) as the oxidant in the presence of a catalytic amount of
copper(II) sulfate (CuSO4) in acetonitrile-water (7:3) (Scheme 2).[22] The influence of
various solvents such as chloroform, dichloromethane, tetrahydrofuran, methanol,
acetonitrile, aqueous methanol and aqueous acetonitrile on the yield of the reaction was
investigated by the authors. However, best results were obtained in aqueous acetonitrile
because of the enhanced solubilizing power of this solvent for the oxidant as well as the
substrate. Here, the use of CuSO4 is the key for high yield of the product because the
yield of the product is significantly enhanced in its presence. The -thiocyanation of
cyclic ketones gave better yields in comparison with acyclic ketones. The best results

were obtained with six-membered rings. The presence of the heteroatom in the sixmembered ring did not affect -thiocyanation.

Simple and efficient protocol for regioselective -thiocyanation of various ketones

possessing -hydrogen by employing ammonium thiocyanate (NH4SCN) in the presence
of N-bromosuccinimide (NBS) in acetonitrile at room temperature under neutral
conditions, which was disclosed by Reddy and co-workers (Scheme 3a-f).[23] In addition,
diethyl azodicarboxylate (DEAD) can also be used for the thiocyanation of enolizable
ketones under mild conditions instead of NBS. The authors have examined the reactivity
of various oxidants, such as PhI(OAc)2, NCS, NBS, NIS, DDQ and Oxone for this
conversion. However, NBS was found to be superior in terms of conversion. Both the
cyclic and acyclic ketones undergoes -thiocyanations in good yields with high
selectivity. Cyclic ketones, such as cyclohexanone, cyclopentanone, cycloheptanone, 2methylcyclohexanone and 4-phenyl cyclohexanone also participated well in this reaction.
Among various solvents, such as acetonitrile, tetrahydrofuran and dichloromethane were
used for this transformation, but acetonitrile proved to be the best solvent for this
transformation. The mechanism shows that, firstly NBS reacts with NH4SCN to generate
electrophilic NTS (N-thiocyanatosuccinimide), then it reacts rapidly with enolizable
ketones to give the desired -thiocyanatoketone derivatives. The superior advantages of
the present methodology are high yields, cleaner reaction condition, operational
simplicity and low cost of the reagents.

An efficient protocol for -thiocyanation of carbonyl compounds was established by

kumar et al. by employing ammonium thiocyanate (NH4SCN) and Ceric ammonium
nitrate (CAN) in the presence of 18-Crown-6 ether as a phase transfer catalyst in
methanol at room temperature afforded high yield of the products (Scheme 4a-e).[24] The
authors have used various solvents like acetonitrile, benzene, dichloromethane, methanol
and ethanol for comparative study. However best results were obtained when methanol
was used as a solvent. The authors have also employed barium thiocyanate, ammonium
thiocyanate and potassium thiocyanate as thiocyanation agent in this reaction. Out of
them barium thiocyanate and ammonium thiocyanate showed good results. Here, CAN
facilitate the oxidative addition of soft base like thiocyanates, which might assistance in
selective and simplistic formation of thiocyanates. The expenditure of 18-Crown-6 ether
as phase transfer catalyst does not have any noticeable effect on the yields of the reaction
but it effects the rate of reaction, when cyclic ketones were used as substrate. While in
case of acyclic ketones, low or negligible products yields were obtained in the absence of
18-Crown-6 ether as phase transfer catalyst. The ring size of cyclic ketones also showing
significant effect on the reaction yields. The best yields were obtained with six member
cyclic ketones. In addition presence of heteroatoms in six member ring does not have any
adverse effect on the product yields. However, exception was 7-hydroxy-2, 2-dimethyl
chromanone, in which the yield of corresponding product was moderate. In addition, five
and seven membered cyclic ketones showing comparatively lower reactivity as compared
to six member cyclic ketones. In general, cyclic ketones shows better efficiency in terms
of product yields and reaction times as compared to acyclic ketones. Moreover, the
authors have observed some side products when reaction was carried out using acyclic

ketones. The authors have also described the possible reaction mechanism, according to
them reaction follows free radical pathway rather than ionic. In this reaction two moles of
CAN are utilized. The one mole of CAN possibly generate tetralone radical, whereas
second mole converts tetralone radical to tetralone cation via oxidation (Path-I, Scheme
4a). Which on reaction with thiocyanate anion gave desired product. In the second route,
CAN possibly generates first tetralone radical and other mole presumably converts SCN
anion to radical (Path-II, Scheme 4a) to gives desired product.

A mild and environmentally benign synthetic protocol was developed by Lenin and coworkers for chemoselective -thiocyanation of enolizable ketones using ammonium
thiocyanate (NH4SCN) in presence of polystyrene cation exchange resin (Amberlyst-15)
in acetonitrile at room temperature (Scheme 5a-c).[25] Both acetophenones and cyclic
ketones were reacted well to give the -ketothionates in very good yields. The reaction
most likely proceeds via the formation of active thiocyanogen (SCN) from Amberlyst-15
and ammonium thiocyanate. The added advantages of the methodology are high
conversions, mild reaction conditions, ease of the isolation of products and simple
experimental procedure.

Bhaleraoet al. have disclosed an efficient and eco-friendly protocol for -thiocyanation of
ketones and -dicarbonyl compounds using a reagent combination of
bromodimethylsulfonium bromide (BDMS) and ammonium thiocyanate (NH4SCN) in
dichloromethane or acetonitrile at room temperature (Scheme 6a-c).[26] The results of
solvent study exposed that dichloromethane and methanol were also feasible for this

transformation; however, in dichloromethane, -bromination was the major product

because the addition of BDMS and NH4SCN are not in sequence. The sequence of
addition was very critical for getting good yields and conversion in this transformation.
Initially acetophenone was reacted with 1.1 equiv. of BDMS and the reaction mixture
was stirred at room temperature until complete consumption of starting material and
formation of corresponding -bromoketone as observed by thin-layer chromotography
(TLC). This was followed by addition of 2.2 equiv. of NH4SCN. By this modification,
the reaction was completed within an overall time and gave of thiocyanatoacetophenone. The protocol was extended to cyclic ketones such as
cyclohexanone and cyclopentanone and corresponding -thiocyanato ketones were
obtained in good yields. The authors have also successfully carried out -thiocyanation of
-dicarbonyl compounds. Under the similar conditions, -thiocyanation of
benzoylacetone, ethyl acetoacetate, and ethyl benzoylacetate proceeded to completion;
however, it was not possible to isolate pure products because of their ready
decomposition into a complex mixture.

The direct and efficient -thiocyanation of ketones with ammonium thiocyanate has been
achieved by Wu et al. using pyridinium hydrobromide perbromide (PHPB) in acetonitrile
as a solvent at room temperature to produce -ketothiocyanates in excellent yields and
with high selectivity (Scheme 7a-e).[27] Several substituted acetophenones reacted rapidly
with ammonium thiocyanate to afford the corresponding 2-thiocyanatoethanone
derivatives. Thus, this method has wide synthetic utility. Mechanistically, the reaction
may proceed via the electrophilic substitution of acetophenone by (+SCN) intermediately

generated in situ from PHPB and ammonium thiocyanate. Use of PHBP as a versatile,
stable, inexpensive, and commercially available reagent is the major advantage of this
protocol.

Wu et al. have developed another protocol of -thiocyanation of various ketones using

ammonium thiocyanate as a thiocyanation reagent and I2O5 as an oxidant in methanol as
a solvent at room temperature, which afforded excellent yield of the products (Scheme
8a-e).[28] The presence of electron donating groups on acetophenone increases the yields
of products. Moreover, various cyclic ketones such as cyclohexanone, cyclopentanone, 1tetralone and indanone also reacted readily with ammonium thiocyanate to give the
corresponding -thiocyanated products in good yields. However, compared with
acetophenone derivatives, aliphatic ketones reacted rapidly to give -thiocyanated
products. Various solvents were examined by the authors in this transformation, however
methanol was found to be most favorable solvent in terms of product yield and reaction
time. To emphasize the effect of the oxidant, various hypervalent iodine oxidants were
subjected to the reaction by the authors. However, satisfactory results were obtained only
with I2O5. Mechanistically, the reaction may proceed via in situ formation of
thiocyanogen (+SCN) from the I2O5 and ammonium thiocyanate. Then it was reacted with
enolizable ketones to give the desired -thiocyanatoketone derivatives.

Kumar and co-workers have developed an efficient and direct approach for the thiocyanation of ketones with -hydrogens using ammonium thiocyanate as a
thiocyanating agent and oxone as an oxidant in methanol at room temperature (Scheme

9).[29] Various cyclic ketones such as cyclohexanone, cyclopentanone, 1-tetralone, and

substituted indanones also reacted readily with ammonium thiocyanate to give the
corresponding -thiocyanated products in excellent yields. Compared to acetophenone
derivatives, aliphatic ketones reacted rapidly to give -thiocyanated products in good
yield. The effect of various solvents on the -thiocyanation of acetophenone was
examined by the authors. However, methanol was the best solvent for this reaction as
compared to other solvents such as acetonitrile, tert-butanol and carbon tetrachloride in
terms of reaction times and product yield. This method offers advantages such as mild
reaction conditions, higher selectivity, operational simplicity and the use of economically
and ecofriendly reagent and catalyst.

Bhalerao et al. have described an efficient and convenient method for -thiocyanation of
ketones and -dicarbonyl compounds utilizing bromodimethylsulfonium bromide
(BDMS) and ammonium thiocyanate (NH4SCN) in acetonitrile to afforded excellent
yield of the products with high selectivity (Scheme 10).[30] In addition, dichloromethane
and methanol were also viable for this transformation; however, in chloroform, brominated product was the major product. Cyclic ketones such as cyclohexanone and
cyclopentanone and corresponding -thiocyanato ketones were obtained in good yields.
In contrast, -substituted -dicarbonyl compounds reacted smoothly to give thiocyanato derivatives. Here, carbonyl compounds firstly underwent bromination
reaction to form -bromo carbonyl compounds, which then rapidly reacted with
ammonium thiocyanate and produce -thiocyanato derivatives. Under the same
conditions, -thiocyanation of benzoylacetone, ethyl acetoacetate, and ethyl

10

benzoylacetate proceeded to completion, however, it was not possible to isolate pure

products because of their ready decomposition into a complex mixture.

Simple and efficient method for regioselective -thiocyanation of various ketones by

employing ammonium thiocyanate (NH4SCN) in the presence of heteropolyacid as a
catalyst in dichloroethane (DCE) at room temperature has been disclosed by Mohan et al.
(Scheme 11).[31] The catalyst could be efficiently recovered from the reaction and reused
several time without loss of their efficiency. Here, HPA not only oxidized the ammonium
thiocyanate to thiocyanogen [(SCN)2] but also enolized the carbonyl group of ketones.
The authors have examined various organic solvents such as dichloromethane,
tetrahydrofuran (THF), dichloroethane, methanol, chloroform, carbon tetrachloride and
acetonitrile. It was observed that maximum yields were obtained when dichloroethane
was used as solvent. Thiocyanation of cyclic ketones occurred with excellent yields,
whereas that of -dicarbonyl compounds occurred in moderate yields. The presence of a
heteroatom in the ring did not affected the yield of -oxothiocyanates.

A simple and rapid protocol has been developed by WU et al. for the -thiocyanation of
ketones by using ammonium thiocyanate (NH4SCN) and SelectfluorTM as a catalyst. The
reaction was carried out in acetonitrile at room temperature to produce ketothiocyanates in excellent yields and with high selectivity. (Scheme 12a-d).[32] The
reactions were completed smoothly within 25 to 75 min, and the products were isolated
by a simple workup procedure. The SelectfluorTM (1-chloromethyl-4-fluoro-1,4diazoniabicyclo[2,2,2]octanebis(tetrafluoro-borate)) is a commercially available, stable,

11

nonvolatile, nonhygroscopic and easy to handle solid and is more widely used for siteselective fluorination of a variety of carbonyl compounds. Various ketones such as
acetophenones, cyclic ketones, and aliphatic ketones all gave regioselective products in
good to excellent yields. A plausible mechanism for this reaction is proposed by the
authors and according to them, the reaction may proceed via the electrophilic substitution
of ketones by in situ generated thiocyanogen (+SCN) from SelectfluorTM and ammonium
thiocyanate. Compare to other catalysts such as Oxone, Heteropoly acids, FeCl3 and
NBS, the reaction was proceeded efficiently in SelectfluorTM.

Liu and co-workers have reported an efficient protocol for the -thiocyanation of ketones
by utilizing ammonium thiocyanate (NH4SCN) and trichloroisocyanuric acid (TCCA) as
a catalyst in acetonitrile at room temperature, which afforded -ketothiocyanates in
excellent yields and with high selectivity (Scheme 13).[33] No chlorination of
acetophenone was observed under the reaction conditions. Acetonitrile appeared to give
the best results compared to other solvents. Mechanistically, the authors assumed that
TCCA reacts initially with ammonium thiocyanate to generate thiocyanogen (+SCN).
Which was react rapidly with ketones to give the desired -thiocyanatoketone.

An efficient and highly selective protocol for the -thiocyanation of ketones was
developed by Yadav and co-workers anhydrous utilizing ammonium thiocyanate
(NH4SCN) and iron(III) chloride (FeCl3) in dichloromethane at room temperature
(Scheme 14).[34] Only, stoichiometric amount of iron(III) chloride was sufficient to
carried out reaction efficiently. However, no reaction was observed in the absence of

12

catalyst, even under reflux over a long reaction time. The authors have tested various
oxidants, such as (diacetoxyiodo)benzene, manganese(III) acetate, and iron(III) nitrate,
anhydrous iron(III) chlorid were found to be the most effective in terms of conversion.
Various metal triflates such as bismuth(III)-, indium(III)-, samarium(III)-, ytterbium(III)-,
and scandium(III) triflate were also found to be ineffective for this conversion. Both an
electron donating and electron withdrawing substituents on acetophenones reacted readily
with ammonium thiocyanate to provide the corresponding -thiocyanato ketones in good
yields. Similarly, cyclic ketones such as 1-tetralone, 2-phenylchroman-4-one,
cyclopentanone, cyclohexanone, 4,4-dimethylcyclohex-2-enone, 2-methylcyclohexanone,
cycloheptanone and cyclododecanone reacted well under similar conditions to give -oxo
thiocyanates. Furthermore, the sterically hindered acyclic ketone and bulky ketone like
tert-butyl methyl ketone and cyclododecanone respectively afforded the corresponding
thiocyanates in good yields. The best conversions were obtained with cyclohexanone
derivatives. The use of inexpensive and readily available iron(III) chloride makes this
procedure simple, convenient, and practical.

An efficient and convenient method for -thiocyanation of carbonyl and -dicarbonyl

compounds was reported by prakash and coworkers by using The combination reagent
(dichloroiodo)benzene and lead(II) thiocyanate in dichloromethane at the 0 oC (Scheme
15).[35] In cases of ethyl acetoacetate and 1H-indene-1,3(2H)-dione, the corresponding
products formed but due to the less stability the products were converted into the
complex mixture during isolation stage.

13

CONCLUSION
This review reveals that the development of various convenient methods for the selective
synthesis of -thiocyanato carbonyl compounds in recent years. Many new thiocyanating
reagents have been explored for improving selectivity, purity, and high yield of the thiocyanato carbonyl compounds. Particularly, ammonium thiocyanate (NH4SCN) is
widely used for -thiocyanation of carbonyl compounds efficiently. It should be noted
that though great progress has been achieved in this field over the last few years. This
research area has still further possibilities for growth and with no doubt, we will see an
increasing number of new methods for -thiocyanation of carbonyl compounds.

FUNDING
R. H. V. is thankful to the University Grants Commission for financial assistance [UGCBSR F.7-74/2007 (BSR)].

ACKNOWLEDGMENTS
The authors are thankful to the Department of Chemistry, Gujarat University,
Ahmedabad, for providing the necessary facilities. UGC-Info net and INFLIBNET
Gujarat University are acknowledged for providing the e-source facilities.

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17

Scheme 1.

18

Scheme 2.

19

Scheme 3.

20

Scheme 4.

21

Scheme 5.

22

Scheme 6.

23

Scheme 7.

24

Scheme 8.

25

Scheme 9.

26

Scheme 10.

27

Scheme 11.

28

Scheme 12.

29

Scheme 13.

30

Scheme 14.

31

Scheme 15.

32