Tetrahedron Letters Vol. 54, Issue 37, 2013
Contents
COMMUNICATIONS
Synthesis of 2-substituted pyrrolidines from nitriles pp 5001–5003
P. Veeraraghavan Ramachandran*, Wataru Mitsuhashi, Daniel R. Nicponski
i) Reductionii) Allylation
ROH
NH2 i) ChlorinationHNR
RCNii) Cyclizationiii) Hydroboration
iv) Oxidation 6 Steps, 18% Yield8 Examples
Used withoutPurification
≈
Easy eco-friendly phenonium ion production from phenethyl alcohols in dimethyl carbonate pp 5004–5006
M. Barontini, I. Proietti Silvestri*, V. Nardi, P. Bovicelli, L. Pari, F. Gallucci, R. Spezia, G. Righi
phenonium ion
O
R R R
S
O
O
CO2, CH3OHS
Amberlyst 15 Up to 95% yield,up to 5 catalytic cycles
S=MeOH, EtOH, TFA, anisole
Selective and sensitive turn on detection of Hg2+ in aqueous solution using a thioether-appended dipeptide pp 5007–5010
Lok Nath Neupane, Keun-Hyeung Lee*
4991
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journal homepage: www.elsevier .com/ locate/ tet le t
An efficient reverse Diels–Alder approach for the synthesis of N-alkyl bismaleimides pp 5011–5013
Venkataramanarao Rao, Suryakiran Navath, Mohankumar Kottur, James R. McElhanon, Dominic V. McGrath*
L-Tartaric acid6 steps
O
N
OOOH
OHN
O
N
OO
Preparation of enantioenriched tetraols and triolamines from a common epoxide pp 5014–5017
Makan Kaviani-Joupari, Michael P. Schramm*
Facile synthesis of thiochromeno[2,3-b]indol-11(6H)-ones and pyrido[30,20:5,6]thiopyrano[2,3-b]indol-5(10H)-ones pp 5018–5021
Mostafa Kiamehr, Firouz Matloubi Moghaddam*, Volodymyr Semeniuchenko, Alexander Villinger, Peter Langer*,Viktor O. Iaroshenko*
X
Cl
O
+
R1 = H, Me, Et, Ph, 7-(CH2)3 R2, R3, R4 = H, FX= CH2, N; Y= Cl, F
Y
R2
R3
R4NR1
S
NR1
S
O
X R4
R3R2K2CO3,
DMF (abs)
Biocatalyzed synthesis of both enantiopure fluoromisonidazole antipodes pp 5022–5025
Wioleta Borzezcka, Iván Lavandera*, Vicente Gotor*
One-pot two-step
FOH
Cl
HN NNO2
N FN
O2N
ON FN
O2N
OH
*
Enan�opureF-MISO
ADHADH
MW
4992 Contents / Tetrahedron Letters 54 (2013) 4991–5000
Highly efficient dynamic kinetic resolution of secondary aromatic alcohols using a low-cost solid super acidas a racemization catalyst
pp 5026–5030
Gang Xu, Liang Wang, Yongjun Chen, Yongmei Cheng, Jianping Wu*, Lirong Yang
Rational design, green synthesis of reaction-based dual-channel chemosensors for cyanide anion pp 5031–5034
Qi Lin, Yong-Peng Fu, Pei Chen, Tai-Bao Wei, You-Ming Zhang*
Arvestolides A–C, new rare sesquiterpenes from the aerial parts of Artemisia vestita pp 5035–5038
Shuaihua Tian, Xingyun Chai, Ke Zan, Kewu Zeng, Xiaoyu Guo, Yong Jiang*, Pengfei Tu*
O O
OHO
AcO
Highly selective recognition of fluoride anion through direct deprotonation of intramolecularly hydrogen-bondedphenolic hydroxyl groups
pp 5039–5042
Xiang Zhang, Jie Fu, Tian-Guang Zhan, Liyan Dai*, Yingqi Chen, Xin Zhao*
N
NN
N
NN
HOO
HOO
OH
OH
F-
N
NN
N
NN
OO
OO
O
O
H
H
Contents / Tetrahedron Letters 54 (2013) 4991–5000 4993
A novel one-pot synthesis of 7-methoxy-2-arylthieno[3,2-b]pyridine-3-ols in domino fashion pp 5043–5047
Srinu Puvvala, Vinod D. Jadhav*, Sheikh M. Farooq, Balaram Patro, Ch. Venkata Ramana Reddy
N
O
O
O
Ar SS Ar
N
O
SAr
OHN
O
N
O1 1A 1C
2
3
N
O
O
N
S ArLDA LDA LDA
THF-78 °C, 2h
A simple and efficient synthesis of 7-methoxy-2-arylthieno[3,2-b]pyridine-3-ols was achieved using a novel one-pot LDA-promoted domino reaction.Although this class of compounds are not very well represented in the literature, similar skeletons are of immense biological importance. A few closely relatedcompounds are reported with multi-step syntheses using harsh conditions and longer reaction time.
Catalyst-free synthesis of 3-hydroxy-3-(alkyl/aryl)indolin-2-ones by addition of organoaluminum reagents to isatins pp 5048–5051
G. Santosh Kumar, Palakuri Ramesh, A. Sanjeeva Kumar, A. Swetha, H. M. Meshram*
NO
O
R
R1
R2
R3
+
1 2
R = H, CH3, BnR1 = H, Cl, BrR2 = H, Cl, Br, I, F, OCF3, NO2R3 = H, Cl, Br
R4 = Me, Et, Ph
3
Toluene
700 CAl(R4)3
No additional catalyst
N
R1
R2
R3
HO R4
O
R
New chalcone dimers from Caesalpinia ferrea Mart act as potent inhibitors of DNA topoisomerase II pp 5052–5055
Susumu Ohira*, Kyouhei Takaya, Taichi Mitsui, Masahiro Kido, Kazuyuki Kakumoto, Ken-ichiro Hayashi, Atsuhito Kuboki,Hiroyuki Tani, Shogo Ikeda, Munekazu Iinuma, Yukihiro Akao, Hiroshi Nozaki*
One-pot esterification-click (CuAAC) and esterification–acetylene coupling (Glaser/Eglinton) for functionalizationof Wang polystyrene resin
pp 5056–5060
Sagi Eppel*, Moshe Portnoy*
4994 Contents / Tetrahedron Letters 54 (2013) 4991–5000
Tandem synthesis of highly functionalized N-phosphorylated sulfonamido-pyrazolone derivatives pp 5061–5063
Issa Yavari*, Manijeh Nematpour
NN
CO2PriCO2
iPr
NN
O
P(O)(OR")2
CO2iPr
HN
R
SO2R'
R
CuI (10 mol%)Et3N, DMFr.t., 5 h, N2
R'S
N3
O O
CRN
SO2R'
P(OR'')3 +DMF, r.t.
Preparation of esters and amides from carboxylic acids and N-formylation of amines promoted by 1,3,5-triazo-2,4,6-triphosphorine-2,2,4,4,6,6-hexachloride (TAPC)
pp 5064–5068
Kiumars Bahrami*, Mohammad M. Khodaei*, Homa Targhan, Mehdi Sheikh Arabi
R COOHR' OH
R' NH2
H COOH RHN R"
(TAPC)P NCl
Cl
3
TAPC
grinding, r.t.
solvent-free, 50 °C
R COOR'
R CONR'
R"RN CHO+
+ 14 examples
16 examples
12 examples
Catalyst-free coupling of indole derivatives with 3,4-dihydroisoquinoline and related compounds pp 5069–5071
István Szatmári, Judit Sas, Ferenc Fülöp*
NH
NH
NH
NH
NH
RR
R
S
R = H, COOHR
NH
NH
NH
NH
MeO
MeO
R
N
MeO
MeO
N N
N
S
Nucleophilic substitution at the alkenyl and cyclopropyl carbon atoms of magnesium carbenoids: a DFT study pp 5072–5074
Tsutomu Kimura*, Tsuyoshi Satoh
Contents / Tetrahedron Letters 54 (2013) 4991–5000 4995
A simple quinoxaline-based highly sensitive colorimetric and ratiometric sensor, selective for nickel andeffective in very high dilution
pp 5075–5077
Shyamaprosad Goswami*, Shampa Chakraborty, Sima Paul, Sandipan Halder, Annada C. Maity
Synthesis of molecular scaffolds assimilating both indolinone and thiazolidinone moieties under environmentallybenevolent conditions
pp 5078–5082
Suman Ray, Chhanda Mukhopadhyay*
S NH
O
S
NH
SiO2 OOO Si S
N
H2O (2 ml) + EtOH (2 ml)Reflux
N
O
O
R1
S N
ON
O
R1
N
Basic ionic liquid promoted heterocyclization to access fused imidazopyridines pp 5083–5086
I. R. Siddiqui*, Shireen, Shayna Shamim, Malik Abdul Waseem, Afaf A. H. Abumhdi, Arjita Srivastava, Anjali Srivastava
N N
H2N [bmIm]OH
r.t., 2-5h N N
N
RRO
O
75-89%
Microwave assisted water mediated benzylic C–H functionalization of methyl aza-arenes and nucleophilicaddition to aromatic aldehydes
pp 5087–5090
N. Nageswara Rao, H. M. Meshram*
N N
OH
R4R4
CHO
R3R3
H2O, MWI
105 0C, 18-40 min
R1
R2
R1
R2
R1 = H, Br, NO2, OMe
R2 = H, NO2
R3 = H, OMe, NO2
R4 =H, OMe, F, Cl, Br, CN, NO2
4996 Contents / Tetrahedron Letters 54 (2013) 4991–5000
Nickel-catalyzed decarboxylative cycloaddition of isatoic anhydrides with alkenes pp 5091–5095
Meng Sun, Yan-Na Ma, Ya-Min Li, Qiu-Ping Tian, Shang-Dong Yang*
N
O
O
OR1
+
NiCl2(PMe3)2 (10 mol %)Zn dust (5 eq.)
toluene, 100 oC, 12 hN
O
R1
R RR2
R3
R2
R3
Asymmetric total synthesis of Tofacitinib pp 5096–5098
Adolfo Maricán, Mario J. Simirgiotis, Leonardo S. Santos*
NO
OH
H
2
N
OH
Boc
6b
N
N
NHMe
NH
7
N
NMe
N
N NH
CN
O
1
In situ slow release of isocyanates: synthesis and organocatalytic application of N-acylureas pp 5099–5102
Atul K. Singh, Ruchi Chawla, Lal Dhar S. Yadav*
R1
O
NH2
TsNBr2
K2CO3, EtOAc, rt NH
NH
R2H2N R2
O
yield 67-94%
O
Ar
ArNu
NuAr
OH
NuH
OH
O OR1
Unprecedented base-promoted nucleophilic addition of diazoesters to nitrones pp 5103–5105
Evelyn Lieou Kui, Alice Kanazawa*, Jean-François Poisson, Sandrine Py*
R1 R2
NR3O
OR4
N2
O
R1 OR4
N
N2
O
R2
HO R3
THF, −78 °C
46−100%, 15 examples
+ LiHMDS
dr 60:40 to > 99:1
Contents / Tetrahedron Letters 54 (2013) 4991–5000 4997
Network of carboxypyranomalvidin-3-O-glucoside (vitisin A) equilibrium forms in aqueous solution pp 5106–5110
Joana Oliveira, Nuno Mateus, Victor de Freitas*
Synthesis of novel 2H,8H-pyrano[2,3-f]chromene-2,8-diones from 8-formyl-7-hydroxy-4-methylcoumarin pp 5111–5114
Ahmed Al-Kawkabani, Baya Boutemeur-Kheddis*, Malika Makhloufi-Chebli, Maamar Hamdi, Oualid Talhi, Artur M. S. Silva*
OHO
O
O
CH3
OO
O
O
CH3
R
Knoevenagel CyclisationHydrolysis
Activated methylene
A new improved method for the synthesis of 2,4-diarylpyrimidines starting from 2,2,2-trichloroethylideneacetophenones
pp 5115–5117
Antonio Guirado*, Enrique Alarcón, Yesica Vicente, Raquel Andreu
Ar1
O
CCl3
Ar2
NH
NH2+ HN N
Ar2
Ar1
HO
CCl3
N NH
Ar2
Ar1 CCl3
HCeneuloT 2Cl2 , H2SO4 THF, t-BuOK N N
Ar2
Ar1
CH3CN, K2CO3N N
Ar2
Ar1
one-pot
p-Methoxybenzyl-N-phenyl-2,2,2-trifluoroacetimidate: a versatile reagent for mild acid catalyzed etherification pp 5118–5121
Nadine Barroca-Aubry*, Mohamed Benchekroun, Filipe Gomes, David Bonnaffé
4998 Contents / Tetrahedron Letters 54 (2013) 4991–5000
Immobilised Candida antarctica B as efficient catalyst for the synthesis of local anaesthetic intermediates pp 5122–5125
Daniela Giunta, Maria Paola Masia, Mauro Marchetti, Raffaele Morrone, Maurizio Solinas*
O OH
R1R2
+ HOR3
O O
R1R2
R3
+ H2O
R1 ,R2 = H, CH3, iPr, Cl, NO2, CF3 ...R3 = H, C5H11, N(CH2CH3)2
cyclohexane40 - 80 °C
Up to quantitative yields
Novozym 435
20 - 24 hours
A facile access to substituted indoles utilizing palladium catalyzed annulation under microwave enhancedconditions
pp 5126–5129
Ranjith P. Karuvalam, Karickal R. Haridas*, Ayyiliath M. Sajith, Arayambath Muralidharan
N
R3
R2N
I
HR3
O+ PdCl2/(A-taphos)
1(a-q) 3(a-q)2(a-q)H
R2R1 R1
Cesium acetateDioxane
microwave, 120 oC
A highly active and efficient catalytic system PdCl2/A-taphos was employed for the synthesis of indoles via palladium catalyzed ring annulation of ortho iodoanilines and aldehydes.
Selective deprotection of TBDMS alkyl ethers in the presence of TIPS or TBDPS phenyl ethers by catalytic CuSO4Æ5H2Oin methanol
pp 5130–5132
Davir González-Calderón*, Luis J. Benítez-Puebla, Carlos A. González-González, Salomón Assad-Hernández,Aydeé Fuentes-Benítez, Erick Cuevas-Yáñez, David Corona-Becerril, Carlos González-Romero*
OR
TBDMSO
OR
HOMW or
20 mol%CuSO4 5H2O
MeOH
R= TIPS or TBDPS
Development of one-pot synthesis of a-hydroxy a-trifluoromethyl amides pp 5133–5136
Zhaoyang Meng*, William E. Butcher
X
1. iPrMgCl, 0 oC
2.F3C
OOMe
O, -78 oC
3. iPrMgcl, HNR2
R1, 0 oC -> rt
F3C
OHN
OR2
R1R
R
one-pot synthesis
Contents / Tetrahedron Letters 54 (2013) 4991–5000 4999
An unexpected one step domino conversion of TMS-alkynes to protected ketones in 4-chromenone system pp 5137–5139
Prabuddha Bhattacharya, Amit Basak*
O
O TMSKF/CH3CN
O
Od4-MeOH O
OCD3
OCD3
OCD3
Calculated mass MNa+: 266.1355 Found: 266.1396
O
OCD3
O Calculated mass MH+: 192.0740 Found: 192.0781
O
O
R
TMS
O
O
R MeOO
82-85%
i i = Ethylene glycol:MeOH 5:1, 45 oC, 16-18 h
5 examples
OTHER CONTENT
Erratum to ‘‘Fluorogenic probes for chemical transformations: 9-anthracene derivatives for monitoring reactionprogress by an increase in fluorescence’’ [Tetrahedron Lett. 54 (2013) 4306–4308]
p 5140
Nobuyuki Mase*, Kunihiko Takabe, Fujie Tanaka*
*Corresponding authorSupplementary data available via ScienceDirect
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5000 Contents / Tetrahedron Letters 54 (2013) 4991–5000