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Tetrahedron Letters Vol. 55, Issue 6, 2014
Contents
DIGEST PAPER
Transition-metal-catalyzed ketone-directed ortho-C–H functionalization reactions pp 1121–1126
Qing-Zhong Zheng, Ning Jiao*
R
O
M: Ru, Rh, Pd, or Ir
H C-H functionalizationR
O
FG
In the past 20 years, organic chemists have made significant contributions to the development of transition-metal-catalyzed ketone-directed ortho-C–H functionalization. Theseinclude Ru, Rh, Pd and Ir-catalyzed ketone-directed C–C and C-heteroatom (O, N, Cl, Br, I) bond forming reactions. This article summarizes the developments of Ru, Rh, Pd andIr-catalyzed ketone-directed ortho-C–H functionalization reactions in the past two decades.
COMMUNICATIONS
LL-Proline catalyzed efficient and convenient synthesis of substituted 2H-chromenes by three-component reaction pp 1127–1131
L. Chandrasekhara Rao, H. M. Meshram*, N. Satish Kumar, N. Nageswara Rao, N. Jagadeesh Babu
O
O
OR
O O
R-OHL-Proline,
RT, 6-8 h
CHO
OHR1
R2
R1
R2
+
R = methyl, ethyl, n-butyl, n-octyl, propargyl,p -methoxy benzylR1 = H, OCH3, R2 = H, Cl, Br, NO2
The trans opening of ethylene diamine tetra acetic acid bis anhydride (EDTAA) with cystine-di-OMe: one-stepsynthesis of bihelical systems
pp 1132–1135
Santhosh Reddy Naini, Subramania Ranganathan*, Jhillu Singh Yadav*, A. V. S. Sarma*, K. V. S. Ramakrishna*,Ramakrishnan Nagaraj*, J. Richard Premkumar, G. Narahari Sastry*
N
N
COOMe
MeOOC
O
SS
NH
(R)
COOMe
(R)MeOOC
HN
O 4
COOMe
MeOOC
MeOOC
COOMeN
N
SS
HN
(S)
(S)
NH
CH3H3C
CH3
H3C
9
O
O
1111
Contents lists available at ScienceDirect
Tetrahedron Letters
journal homepage: www.elsevier .com/ locate/ tet le t
Keggin-type Bronsted dodecatungstophosphoric acid: a quasi homogenous and reusable catalyst system for liquidphase Beckmann rearrangement
pp 1136–1140
Gagandeep Kaur, Jaspreet Kaur Rajput*, Priya Arora, Nisha DeviEfficient
Clean
SimpleRecyclable
GreenC NOH
nC NOH
R
R'
n = 0, X = S, R" = CH3
n = 1, X = N, R" = CH2CH3
n = 0, 1
NH
OnC N
R'
OR
H
X
nC
R''
NOHX
n
HN
R''
O
R=C6H5, R’=C6H5
R=4- Cl-C6H4, R’=C6H5
R=C6H5, R’=CH3
R=4-Cl-C6H4, R’= CH3
R=2-OH-C6H4, R’= CH3
R=4-OCH3-C6H4, R’= CH3
R=4-CH3-C6H4, R’= CH3
R=4-NO2-C6H4, R’= CH3
H3PW12O40
Refluxing, CH3CN
0.05mmol
Beckmann rearrangement of ketoximes to N-substituted amides and lactams using dodecatungstophosphoric acid (DTPA).
Pd(II)-catalyzed deprotection of acetals and ketals containing acid sensitive functional groups pp 1141–1144
Francisco Juliá-Hernández, Aurelia Arcas, José Vicente*
Stereoselective synthesis of the right-hand segment of tubiferal A pp 1145–1147
Takahiro Hiramatsu, Motomasa Takahashi, Keiji Tanino*
Tubiferal A
CN
AcO OMOMO
OMe
OMe
MOMO
O
O
H
HH
O
O
HO
HO
H
H
HO H
H
H
A practical and efficient synthesis of 6-carboalkoxy-13-cycloalkyl-5H-indolo[2,1-a][2]benzazepine-10-carboxylic acidderivatives
pp 1148–1153
Piyasena Hewawasam*, Yong Tu, Thomas W. Hudyma, Xiaofan Zhang, Robert G. Gentles, John F. Kadow, Nicholas A. Meanwell
MeO
OP(OMe)2
O
11 6a
NMeO2C
CO2Me
Cs2CO3, DMF60 °C, 3h; 96%
HN
CHOMeO2C
12
1112 Contents / Tetrahedron Letters 55 (2014) 1111–1119
Synthesis of 4-aryl-6-indolylpyridine-3-carbonitriles and evaluation of their antiproliferative activity pp 1154–1158
Naglaa Salem El-Sayed, Amir Nasrolahi Shirazi, Magda Goda El-Meligy, Ahmed Kamel El-Ziaty, David Rowley, Jiadong Sun,Zenat Adeeb Nagib*, Keykavous Parang*
NH
ArCN
O
NH 13a-e
N
ArCN
X
NHX = -Cl 14a-e
X = -NH(CH)2NH2 15a-e
Synthesis of imidazo[1,2-a]pyridine in the presence of iodine–water catalytic system pp 1159–1163
I. R. Siddiqui*, Pragati Rai, Rahila, Anushree Srivastava, Shayna Shamim
N
NH2 CHON
NI2 (10mol%)
water /600C6.0-6.5h65-87%
R1R2 R3
R1R2
1(a-d) 2(a-h) 3(a-b)5(a-m)R3
Studies directed toward the synthesis of caylobolide A: convergent synthesis of C21–C40 subunit pp 1164–1167
J. S. Yadav*, N. Swapnil, M. Venkatesh, A. R. Prasad
O
OOHOHOH
HO
HO
OH OH OH OH
OTBS
OTBS
OHOHOBn
BnO
Caylobolide A
An efficient and regioselective one-pot multi-component synthesis of pyrimido[4,5-d]pyrimidine derivatives in water pp 1168–1170
Swarup Majumder*, Pallabi Borah, Pulak J. Bhuyan*
NCS
X
ArCHO N
N
H2N
O
OR
+ + N
NH
N
N
O
OR
Ar
S
X
p-TSA
Water,Reflux
1-2h1 2 3 4
X=H, CH3 R=H, CH3
Contents / Tetrahedron Letters 55 (2014) 1111–1119 1113
Reaction-based colorimetric and fluorogenic signaling of hydrogen sulfide using a 7-nitro-2,1,3-benzoxadiazole–coumarin conjugate
pp 1171–1174
Jihee Bae, Jiyoung Choi, Tae Jung Park, Suk-Kyu Chang*
First total synthesis of prunustatin A pp 1175–1177
Shuhei Yamakoshi, Eiji Kawanishi*
O
O OO
O O
BocHN
O
HOCO2H
Ph
Prunustatin A
OHCPh
OBnOtBuO2C
OBr
HO
CO2SEMBocHN BnO
CO2H
Macrocyclization (C5-O4 bond)
Reformatsky reaction
O
O OO
O
O
O
Ph
O
OHN
O
OHNHCHO
4
5
Synthesis of 1,6-dihydropyrimidines via copper-catalyzed multistep cascade reactions between O-propargylicaldoximes and isocyanates
pp 1178–1182
Itaru Nakamura*, Toshiki Onuma, Dong Zhang, Masahiro Terada
N NO
R2
R1
N
R3
O • NTs
+
R3
Ts
R2 R1
cat. CuBr / SPhos
− CO2
H
H
An expedient synthesis of 3-alkylideneoxindoles by Ti(OiPr)4/pyridine-mediated Knoevenagel condensation pp 1183–1187
Hyun Ju Lee, Jin Woo Lim, Jin Yu, Jae Nyoung Kim*
NO
H
Ph
O
Ti(OiPr)4 Me
NOTi(OiPr)3
H
H
NO
H
Me Ph
NO
H
Ph Me
+
Z (78%) E (15%)
pyridine
H H
1114 Contents / Tetrahedron Letters 55 (2014) 1111–1119
Aerobic oxidative desymmetrization of meso-diols with bifunctional amidoiridium catalysts bearing chiralN-sulfonyldiamine ligands
pp 1188–1191
Junki Moritani, Yasuharu Hasegawa, Yoshihito Kayaki, Takao Ikariya*
cat
NIr
N
H
C6H5
C6H5
Mscatair, 1 atmTHF30 °C
+ 1/2 O2 + H2O
O
OH
OH
OH
n n
S/C = 10[diol] = 0.1 Mn = 1–3
up to 99% yieldup to 99% ee
Synthesis of 1-acetyl-2-silyoxycycloheptane derivatives via highly stereoselective formal [5+2] cycloaddition reaction pp 1192–1195
Mami Kudo, Fumikatsu Kondo, Hideki Maekawa, Tadashi Shimizu, Masaaki Miyashita, Keiji Tanino*
Thionium ion promoted Michael acceptor: a sequence of Pummerer/Michael reactions for the stereoselective synthesisof 5-(1-(arylthio)vinyl)-oxazolines
pp 1196–1198
Shimin Xu, Qianyun Zhang, Hongwei Zhou*
HN
SAr
O
R2
CF3
O
R1
OHN
SAr
O
R2 S
ON
R1
R2R1
O
ArDCM, -20 oC
TFAA
up to 85% yield
Pd/C: an efficient and heterogeneous protocol for oxidative carbonylation of diols to cyclic carbonate pp 1199–1202
Sujit P. Chavan, Bhalchandra M. Bhanage*
+HO OH
CO
R1
OO
R2
O
R2R1
R1, R2 = -H, -Alkyl, -Ph-CH2Cl, -CH2OAr
KI, NaOAc
Pd/C
O2, DME3-8 h
The present protocol involves highly efficient and practical approach for the synthesis of cyclic carbonates via oxidative carbonylation of diols, glycerol andits derivatives using Pd/C as heterogeneous and recyclable catalyst.
Contents / Tetrahedron Letters 55 (2014) 1111–1119 1115
Synthesis of 9-oxiranyl-9H-purine derivatives in b-cyclodextrin cavity pp 1203–1206
Qian Zhang*, Yong-Zhen Huang, Jun-Hui Yang, Bai-Wei Ma, Gui-Rong Qu, Hai-Ming Guo*
N
NN
NR1
Oxone
R2
R
N
NN
NR1
R2
R O
β -CD, OO
OHHO
OH
β -CD
H2O, RT
Synthesis of benzofuran-containing spirolactones from diarylcyclopropenones pp 1207–1211
Jia-Ru Syu, Chi-Hui Lin, Chiao-Wen Kuo, Ding-Yah Yang*
OOMeOMe
MeO O
O Ph
PhPh Ph
O
MeO
O
O
O
O Ph
Ph
cat. CuBr
An efficient route for the construction of a novel benzofuran-containing spirolactone skeleton via copper-catalyzed heterodimerization of1,2-diarylcyclopropenones followed by sequential demethylations of highly strained cyclopropene-derived spirolactones is reported.
One-pot synthesis of aryl alkyl thioethers and diaryl disulfides using carbon disulfide as a sulfur surrogate in thepresence of diethylamine catalyzed by copper(I) iodide in polyethylene glycol (PEG200)
pp 1212–1217
Habib Firouzabadi*, Nasser Iranpoor*, Arash Samadi
Na
Et2N
SS
(ii) ArZ, CuI (10 mol%) PEG200, 110 -130 °C
(iii) KOH, H2OEt2NH + CS2
ArSSAr
r.t.
(i) NaOH(aq)
ArSRRBr
HCl (conc)
( 30 examples)
( 6 examples)
Z = I, OTs, Br, Ar = phenyl, 4-methylphenyl, 4-methoxyphenyl, naphthalen-1-yl, 4-trifluoromethylphenyl, 3,4-dichlorophenyl, R = benzyl, n-butyl, cyclohexyl.
Elongation of the molecular probe DDNP with phenylethynylidene or phenyldiazenylidene spacers pp 1218–1221
Luka Rejc, Jan Fabris, Armin Adrovic, Marta Kasunic, Andrej Petric*
N
NN
NN
N
NN
N
NN
DDNP 105
1116 Contents / Tetrahedron Letters 55 (2014) 1111–1119
Synthesis of tris(b,b,c-oximinoalkyl)amines from aliphatic nitro compounds and methyl vinyl ketone pp 1222–1225
Elena A. Shalamova, Yeosan Lee, Garam Chung, Artem N. Semakin*, Jinho Oh, Alexey Yu. Sukhorukov*, Dmitry E. Arkhipov,Sema L. Ioffe, Sergey E. Semenov
N(OTMS)2
R3
N
R2N
OH
R3
N OHR1
NR4O
N(OTMS)2
R2O
R1
R4O NH2
[NH3]
A green and convenient protocol for the synthesis of novel pyrazolopyranopyrimidines via a one-pot, four-componentreaction in water
pp 1226–1228
Majid M. Heravi*, Farnoush Mousavizadeh, Nazanin Ghobadi, Mahgol Tajbakhsh
Chemoselective aminomethylation of bifunctional substrates: carbonyl versus phenolic hydroxyl, carbonyl versuspyrazole and pyrrole versus phenolic hydroxyl as competing activating groups
pp 1229–1233
Gheorghe Roman*
OH
CH3
O
or
Ar
O
NN
CH3
CH3
NHO
H3C
H3C
Formation of dilithiated bis-(1H-pyrazol-1-yl)alkanes and their application in the synthesis of diboronic acids pp 1234–1238
Krzysztof Durka, Agnieszka Górska, Tomasz Klis*, Janusz Serwatowski, Krzysztof Wozniak
N N
N N
(CH2)
1. t-BuLi, -78 °C, THF2. B(OEt)3
3. H3O+
n
Br
Br
N N
N N
(CH2)n
Br
Br
X
X
X = CONHt-Bun = 1,2,3,8
1. LDA, -78 °C, THF2. t-BuNCO3. H3O+
N N
N N
(CH2)n
B(OH)2
B(OH)2
X
X
X = CONHt-Bu
Contents / Tetrahedron Letters 55 (2014) 1111–1119 1117
Azo-coupling of pyrazole-3(5)-diazonium chlorides with cyanothioacetamide: a convenient synthesis ofpyrazolo[5,1-c][1,2,4]triazine-3-carbothioamides
pp 1239–1242
Irina V. Ledenyova*, Vitaly V. Didenko, Victor V. Dotsenko, Khidmet S. Shikhaliev
N
R Ar
HN N N
Cl
H2NNS
N
R Ar
N NN
H2NNH2S
Hantzsch-typeproducts
Oxidationproducts
Synthesis of chiral butenolides using amino-thiocarbamate-catalyzed asymmetric bromolactonization pp 1243–1246
Chong Kiat Tan, Jun Cheng Er, Ying-Yeung Yeung*
R2
R1
O
OHR2R1
OO
1. NBSCHCl3/hexane (1:1), -78 oC2. Et3N, 5 min
N
HN
O
S
NH
(10 mol%)
up to 99% yield58% ee
Synthesis of phosphorus containing medium ring heterocycles by sequential Claisen rearrangement and ring closingmetathesis
pp 1247–1250
K. C. Majumdar*, Raj Kumar Nandi, Sintu Ganai
O PO OEt
n = 0, 1n RCM Protocol
Aromaticor
Heterocycles
Aromaticor
Heterocycles
POO OEt
n
14 examples(65-92%) Phosphorus heterocycles
OHAromaticor
Heterocycles
A one-pot multicomponent synthesis of polysubstituted thiophenes via the reactions of an isocyanide, a-haloketones,and b-ketodithioesters in water
pp 1251–1254
Firouz Matloubi Moghaddam*, Mohammad Reza Khodabakhshi, Arash Latifkar
SMeS
O
R
O
Ar
O S
SMe
NC ,
RO Br
2)
1)
H2O, 6 h
, K2CO3, 6 h
Ar
1118 Contents / Tetrahedron Letters 55 (2014) 1111–1119
Synthesis of an azabicyclic framework towards (±)-actinophyllic acid pp 1255–1257
Danny Mortimer, Matthew Whiting, Joseph P. A. Harrity*, Simon Jones*, Iain Coldham*
NH
OTBS
NBoc
CO2Me
CO2MeCHO
BPh3 / H2Otrifluorotoluene
CO2MeCO2Me
HN
HH
O
NBoc
A ‘turn-on’ fluorescent chemosensor based on rhodamine-N-(3-aminopropyl)-imidazole for detection of Al3+ ions pp 1258–1262
Zhengqiang Li, Qiuping Hu, Chunxiao Li, Jintao Dou, Jiaojie Cao, Weikai Chen, Qingzeng Zhu*
*Corresponding authorSupplementary data available via ScienceDirect
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Contents / Tetrahedron Letters 55 (2014) 1111–1119 1119