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Tetrahedron Letters Vol. 54, Issue 8, 2013 Contents COMMUNICATIONS Nano copper oxide mediated ligand-free C–S cross-coupling and concomitant oxidative aromatization of 4-aryl-3,4-dihydropyrimidin-2(1H)-thione with diaryliodonium salts pp 739–743 Bhagyashree Y. Bhong, Amol V. Shelke, Nandkishor N. Karade* N N R 1 S R 2 O I OTf nano CuO (10 mol %) K 2 CO 3 (2.5 equiv) DMF, reflux, 12 h R 3 R 3 63-84% yield, 16 examples R 3 N H NH S R 1 R 2 O Penicolinates A–E from endophytic Penicillium sp. BCC16054 pp 744–748 Chakapong Intaraudom, Nattawut Boonyuen, Rapheephat Suvannakad, Pranee Rachtawee, Pattama Pittayakhajonwut* N H 3 CO O N OR O n N H 3 CO O CH 3 R 1 R 2 Efficient synthesis and X-ray structures of new a-quinolin-3-yl-a-aminonitriles and derivatives pp 749–752 Souheila Ladraa, Fabienne Berrée, Abdelmalek Bouraiou, Sofiane Bouacida, Thierry Roisnel, Bertrand Carboni, Ali Belfaitah* N Cl CHO R N H O R NH 3 Cl COOCH 3 N Cl R NHR' CN + - 719 Contents lists available at SciVerse ScienceDirect Tetrahedron Letters journal homepage: www.elsevier.com/locate/tetlet

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Tetrahedron Letters Vol. 54, Issue 8, 2013

Contents

COMMUNICATIONS

Nano copper oxide mediated ligand-free C–S cross-coupling and concomitant oxidative aromatization of4-aryl-3,4-dihydropyrimidin-2(1H)-thione with diaryliodonium salts

pp 739–743

Bhagyashree Y. Bhong, Amol V. Shelke, Nandkishor N. Karade*

N

N

R1

S

R2

OI

OTf

nano CuO (10 mol %)K2CO3 (2.5 equiv)

DMF, reflux, 12 hR3R3

63-84% yield, 16 examplesR3N

H

NH

S

R1

R2

O

Penicolinates A–E from endophytic Penicillium sp. BCC16054 pp 744–748

Chakapong Intaraudom, Nattawut Boonyuen, Rapheephat Suvannakad, Pranee Rachtawee, Pattama Pittayakhajonwut*

NH3CO

O

NOR

O

n

NH3CO

O

CH3

R1 R2

Efficient synthesis and X-ray structures of new a-quinolin-3-yl-a-aminonitriles and derivatives pp 749–752

Souheila Ladraa, Fabienne Berrée, Abdelmalek Bouraiou, Sofiane Bouacida, Thierry Roisnel, Bertrand Carboni, Ali Belfaitah*

N Cl

CHO

R NH

ORNH3 Cl

COOCH3

N ClRNHR'

CN+ -

719

Contents lists available at SciVerse ScienceDirect

Tetrahedron Letters

journal homepage: www.elsevier .com/ locate/ tet le t

Page 2: Graphical contents list

Tuning the solubility of hepta(p-benzamide)s via the monomer sequence pp 753–756

Helga Seyler, Andreas Kilbinger*

Structurally diversified products from the reactions of 2-aminobenzamides with 1,3-cyclohexanedionescatalyzed by iodine

pp 757–760

Lian Lu, Mei-Mei Zhang, Hong Jiang, Xiang-Shan Wang*

NHR1

O

NH2

RNHR1

O

NHR

1

I2, 50 oC

R3

R2

O

N

O

NR

R1

R3

R2

O

80 oC

R1 = H

NH

O

NR

R3

R2

HN

HN

O

R

R3

R2

O

O

2

3 or 6

4

5

I2, 110 oC1

2

I2, 110 oC

I2

Controlling the reaction temperature at 50 �C, 80 �C, and 110 �C, respectively, the iodine-catalyzed reaction of 2-aminobenzamides with 1,3-cyclohexanedionesgave structurally diversified products. In the latter, it gave bis-quinazolin-4(3H)-ones unexpectedly, with 1,3-cyclohexanediones ring-opening.

A simple one-pot method for the mercuric oxide mediated synthesis of piperazines via oxidative diaminationof olefins

pp 761–764

Harpreet Kour, Satya Paul*, Parvinder Pal Singh, Monika Gupta, Rajive Gupta

R

R1

R2HN

R2HNHgO. 2HBF4

NR2

R2NR1

R

An efficient ecofriendly protocol for the synthesis of novel fluoro isoxazoline and isoxazolidines using N-benzylfluoro nitrone via cycloaddition reactions

pp 765–770

Bhaskar Chakraborty*, Govinda Prasad LuitelC6H5CH2NHOH

N

O H

R1 R2

Bn

R

12

3

45RCHO

[bmim]BF4 [bmim]BF4

R = 2,6 difluro/ 2 fluoro/ 3,4 difluoro/ 4 fluoro/ 2 hydroxy/ 4 hydroxy benzene/ Ph ; Bn = C6H5CH2

R1 = Ph ; R2 = COOCH3

R1 = R2 = COOCH3

R1 = R2 = COOHR3 = Et ; Ph ; R4 = H etcR3 = R4 = Ph ; R3 = Me ; R4 = Ph etc X = Cl/Br/I

+

SN2

R3CHO / R3R4CO

CR3

R4X

H

R

C

H

N+

Bn-O

R

C

H

N Bn

Hydrolysis

+ BnNH2RCHO

R2R1

CH3

CHO

[bmim]BF4

N

O H

Bn

R

12

3

45

H3CCHOendo

1-Butyl-3-methylimidazolium based ionic liquids are found to accelerate significantly the intermolecular 1,3-dipolar cycloaddition of N-benzyl fluoro nitronesderived in situ from aldehydes and benzylhydroxylamine, with electron deficient alkynes to afford enhanced rates and improved yields of isoxazolines whilewith enals exclusively endo isoxazolidines are obtained with high selectivity. Synthetic potentiality of the novel isoxazolines and nitrones has also been testedsuccessfully.

720 Contents / Tetrahedron Letters 54 (2013) 719–737

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Selective fluorescence sensor for Al3+ and Pb2+ in physiological condition by a benzene based tripodal receptor pp 771–774

Barun Kumar Datta, Chirantan Kar, Arghya Basu, Gopal Das*

Fmoc-aza-b3-Lys-OAllyl and Fmoc-aza-b3-Asp-OAllyl for on-resin head-to-tail cyclization of aza-b3-peptides pp 775–778

Shoukri Abbour, Michèle Baudy-Floc’h*

NH

NHN

HN

N

HN

NH

NNH

H2N

O

OO

OO

NH

PbfN NHPbf

BocHN

NTrtN

O

O

NBoc4 3

4

OH

O

head to tail cyclization

FmocNH

NO

OH2N

4

Fmoc-Aza-β3-Lys-OAllyl

FmocNH

NHN

4

O

O NH

NHN

HN

N

HN

NH

NNH

HN

Fmoc

O

OO

OO

NH

PbfN NHPbf

BocHN

NTrtN

O

O

NBoc4 3

4

O

O

Luminescent biscyclometalated iridium(III) complex for selective and switchable Cu2+ ion binding in aqueous media pp 779–782

Fengniu Lu, Masaki Yamamura, Tatsuya Nabeshima*

Stereochemistry of theonezolides A–C pp 783–787

Kohei Nozawa, Masashi Tsuda, Naonobu Tanaka, Takaaki Kubota, Eri Fukushi, Jun Kawabata, Jun’ichi Kobayashi*

HO

CH3

CH3

OH

O O

NH

CH3O

CH3

CH3

HO3SO

O

OH

HO

HO

OH

CH3

OH OH OH OH OH OH O

CH3

SN

H3C

NH2

16

14

10

8 41

34

3536

33

19

28

2422

44 9574 4945 55 5753

63

60

SRS

S

S

S

R

R

SS

S

R

S

R SS

S

S

S

theonezolide A (1): n = 2theonezolide B (2): n = 1theonezolide C (3): n = 3

n

O

N

Contents / Tetrahedron Letters 54 (2013) 719–737 721

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One-pot synthesis of bis(amino)-1,2,4-thiadiazoles via direct SNAr pp 788–791

Howard A. Beeley, Sébastien Degorce, Craig S. Harris*, Jonathan Lecoq, Rémy Morgentin, David Perkins

SN

NCl

ClS

NN

NH

NH

R1

R2

ZnCl2

DIPEAcyclohexanol,r.t. to 80 °C

R2NH2

R1NH2

One-pot

90-120 °C

The synthesis of bis(amino)-1,2,4-thiadiazoles usually relies on a four step sequence. Herein, we communicate to our knowledge the first one-potsynthesis of bis(amino)-1,2,4-thiadiazoles via a double SNAr approach.

Synthesis of dibromoolefins via a tandem ozonolysis–dibromoolefination reaction pp 792–795

Brenna Arlyce Brown*, Jonathan G. C. Veinot

Novel calix[4]arene-based receptors with bis-squaramide moieties for colorimetric sensing of anionsvia two different interaction modes

pp 796–801

Can Jin, Man Zhang, Chao Deng, Yangfan Guan, Jun Gong, Dunru Zhu, Yi Pan, Juli Jiang*, Leyong Wang

OHOH OO

NH HN

N N

O

O O

O

NO2 O2N

OHOH OO

NH HN

NH HN

O

O O

O

Anion H-bond modeAcid-base mode

A = F-, AcO-, H2PO4-

Anion

2 [HA2]-

Reactivity of 1-aminoazetidine-2-carboxylic acid during peptide forming procedures: observation of an unusualvariant of the hydrazino turn

pp 802–805

Amandine Altmayer-Henzien, Valérie Declerck, Régis Guillot, David J. Aitken*

722 Contents / Tetrahedron Letters 54 (2013) 719–737

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A Europium-based luminescent chemosensor for Zn2+ with quinoxaline as the antenna pp 806–810

Xinxiu Fang, Guiyan Zhao, Yanmeng Xiao, Jingwei Xu*, Wei Yang*

Facile conversion of chromane-6-triflate to chromane-6-alanines under palladium conditions pp 811–813

Daniel K. Miller*

OR"

MeO2C NHBoc

OR"

TfO

Benzothiazines in organic synthesis: formation of a cyclopropane via neighboring group participation pp 814–816

Zhengxin Cai, Michael Harmata*

NS O

Ph

H

H

Me

OMe

H

NS O

HMe

OMe

Me MeOMs

4 equiv. imidazoleDCM, 50 °C, overnight

91%Ph

Me

The phosphorus-Claisen condensation pp 817–820

Laurent Gavara, Fabien Gelat, Jean-Luc Montchamp*

Contents / Tetrahedron Letters 54 (2013) 719–737 723

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Synthesis of 3-spiropyrrolidine-3-spirooxindoles from Baylis–Hillman adducts of chromone with azomethine ylidesvia [3+2] cycloaddition reaction

pp 821–827

Panneerselvam Yuvaraj, Boreddy S. R. Reddy*

O

O OH

NH

O

OO

N

NH

NCO

ON

NH

NC O

1a- j 2a- j major 4a- j minor 5a- j

CN R R

R1

R sarcosine (3)HOO

R1

R1

OHO

CH3CN, 8 hreflux

3-Spiropyrrolidine-oxindole unit is a privileged heterocyclic motif forming the core of a large family of alkaloid natural products with strong bioactivityprofile and interesting structural properties. A novel regioselective synthesis of functionalized 3-spiropyrrolidine-3-spirooxindoles from 4-oxo-4H-chromone derivatives was accomplished by the [3+2] cycloaddition of azomethineylides with Baylis–Hillman adducts.

Concise and protecting group-free synthesis of botryolide-E pp 828–829

D. Chandra Rao, D. Kumar Reddy, V. Shekhar, Y. Venkateswarlu*

OOAc

O

OMe O

O

HO O

O

162

A short and straightforward approach towards 6-amino and 6-aminoalkyl thiazolo[4,5-c]pyridazines pp 830–833

Alessandro Stella, Steven De Jonghe, Kenneth Segers, Piet Herdewijn*

Selectivity control by silver catalysts in the cycloisomerization of 1,6-enynes derived from propiolamides pp 834–839

Jaeyoung Koo, Hyun-Sub Park, Seunghoon Shin*

R'NR M = Ag

O

R'N

H

R

O

RT R'N

H

OR

M+

R'NR

MO

R'N

OR''

(R = CH2R'')

R'N

O

(R = Ph)

R'NR

MO

724 Contents / Tetrahedron Letters 54 (2013) 719–737

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Complexation to [Ru(bpy)2]2+: the trick to functionalize 3,30-disubstituted-2,20-bipyridine pp 840–842

Pascal Guillo, Olivier Hamelin*, Jacques Pécaut, Stéphane Ménage

N

N

N

NN

NRu

OH

OH N

N

N

NN

NRu

R

R

2+ 2+

R = Br, N3, Phthalimide

A catalytic, mild and efficient protocol for the C-3 aerial hydroxylation of oxindoles pp 843–846

Benjamin R. Buckley*, Beatriz Fernández D.-R.

Intramolecular cyclization of N-propargylic b-enaminones catalyzed by silver pp 847–849

Marcos A. P. Martins*, Marcelo Rossatto, Clarissa P. Frizzo, Elisandra Scapin, Lilian Buriol, Nilo Zanatta, Helio G. Bonacorso

R2

O

N

R1

R H

AgNO3

NR

R1

O

R2

NR

MeO

R2

R1

R = PrR1 = MeR2 = CF3

+

24h, 30°C 12h, 25°C

R = Pr, Bn, Ph, 4-Me-C6H4R1 = Me, Et, PrR2 = CF3, CO2Et

80% 75-90%

1,2,3-Triazoles as leaving groups in purine chemistry: a three-step synthesis of N6-substituted-2-triazolyl-adeninenucleosides and photophysical properties thereof

pp 850–853

Armands Koval�ovs, Irina Novosjolova, Erika Bizdena, Inga Biz�ane, Lina Skardziute, Karolis Kazlauskas, Saulius Jursenas,M�aris Turks*

RN

N

N

N

N3

N3N

N

N

N

N

N

NN

NN

R

R

N

N

N

N

Nu

N NN

RSugar

1 2 3

Sugar Sugar

NuH

280 nm 400 nm

Contents / Tetrahedron Letters 54 (2013) 719–737 725

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Synthesis of highly efficient pH-sensitive DNA cleaving aminomethyl N-substituted cyclic enediyne andits L-lysine conjugate

pp 854–857

Ishita Hatial, Partha S. Addy, Ananta K. Ghosh, Amit Basak*

NH2

NH3

2 CF3COO

NH2R

3 CHF3CHOONH2

CF3COO

1 2 3

Lanes 1: DNA alone, 2: at pH 7.5, 3: at pH 6.5 and 4: at pH 5.5

1 2 3 4 1 2 3 4 1 2 3 4

Compound 1 Compound 2 Compound 3

HN

O

NH3

H3N

NH2R

3 CF3COOR =

NH2

NH3

2 CF3COO

Form II Form III Form I

An addition of benzylic sp3 C–H to electron-deficient olefins pp 858–860

Hong-Ying Li, Li-Juan Xing, Tong Xu, Peng Wang, Rui-Hua Liu*, Bin Wang*

NN

EWG

EWG

NN

EWG

EWG+ 100-120 °C

DMSOR R

catalyst-freeadditive-free

Convenient synthesis of multivalent zinc(II)–dipicolylamine complexes for molecular recognition pp 861–864

Shuzhang Xiao, Serhan Turkyilmaz, Bradley D. Smith*

HN

HN

SNN

N

N

N

N

NH

NHS

N

N

N N

NN

NH N

H

S NN

N

N

N

N

HN

HN S

N

N

NN

NN

H2N NH2

NH2H2N

O

N

NN

NN

N

NCS

conjugation

Use of iodine for efficient and chemoselective glycosylation with glycosyl ortho-alkynylbenzoates as donorin presence of thioglycosides

pp 865–870

Samrat Dutta, Swarbhanu Sarkar, Shyam Ji Gupta, Asish Kumar Sen*

R2OH

I2, CH3CN

OPOOR2

O

IR1

OOPOO R1O

Chemoselectively activable inpresecne of Thioglycoside

726 Contents / Tetrahedron Letters 54 (2013) 719–737

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SN2 substitution reaction of 2-C-acetoxymethyl glycals catalyzed by iodine: a novel synthesis of 2-C-N-arylamidomethylglycals

pp 871–873

J. S. Yadav, G. Narasimhulu, N. Umadevi, Y. Vikram Reddy, B. V. Subba Reddy*

O

ROOR

ROOAc

O

ROOR

RO

+5 mol% I2

NHTs

CH2Cl2, r.t.

R = benzyl or ethyl

NTs

Construction of novel steroidal isoxazolidinone derivatives under Vilsmeier–Haack conditions pp 874–877

Shamsuzzaman*, Hena Khanam, Ashraf Mashrai, Nazish Siddiqui

H

H

H

X

H

H

H

X

H

H

H

COO

HNXHO H N

OH

NH2OH.HCl/CH3COONa

C2H5OH/reflux, 4 h

DMF/POCl3

stirring at 0 C for 15 min,then at 60-65 C°

°

X X X

OAc (1) OAc (4) OAc (7) Cl (2) Cl (5) Cl (8) H (3) H (6) H (9)

An efficient, ionic liquid mediated one-pot, three component sequential synthesis of 3-benzothiazolyl-2-styrylquinazolin-4(3H)-ones

pp 878–882

Mahendra Kumar*, Kailash Sharma, Dinesh Kumar Sharma, Anand Kumar Arya

N

O

O

CH3

S

NNH2

Me

N

N

O

CH3

S

N Me

1

2a

3

CHO

OMe4a N

N

O

S

N Me

5aOMe

SFILs, 80 °C SFILs, 80 °C

An efficient and diversity oriented one-pot three component sequential synthetic method has been presented for the synthesis of 3-benzothiazolyl-2-styrylquinazolin-4(3H)-ones. The synthetic method involves the reaction of 3,1-benzoxazinone with 2-aminobenzothiazole and subsequently with aromatic aldehyde using SO3H-functionalized ionicliquids (SFILs) as solvent/catalyst.

Efficient synthesis of (R)-ochratoxin alpha, the key precursor to the mycotoxin ochratoxin A pp 883–886

Cesar Antonio Lenz, Michael Rychlik*

Cl

O

OH

OR

Cl

O

O

OR

OH

O

OO

OH

Cl

O

1) LTMP, THF-50 °C, 4h

2)

-50 °C, 1hRoute A: R = HRoute B: R = CO2H

Route A: 3 steps

Route B: 1 step

(R)-Ochratoxin α

20.7 % overall yield

15.4 % overall yield

Contents / Tetrahedron Letters 54 (2013) 719–737 727

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Gelsochalotine, a novel indole ring-degraded monoterpenoid indole alkaloid from Gelsemium elegans pp 887–890

Shuang Liang*, Chun-Yong He, László F. Szabó, Yi Feng*, Xiao Lin, Yuan Wang

3 1520

167 4

6

14

17

1819

5

21

22

NO

OOMe

OH

H

H

H

N-Alkylation of tosylhydrazones via a metal-free reductive coupling procedure pp 891–895

Jin-Biao Liu, Hui Yan, Gui Lu*

Ar N

R HN

Ts

NaOMe, MeOH

50 °C, 12-48 h Ar N

RN

Ts

Ar R

2

Synthesis of 5-aryl-3H-[1,3,4]oxadiazol-2-ones from N0-(chloro-aryl-methylene)-tert-butylcarbazates usingbasic alumina as an efficient and recyclable surface under solvent-free condition

pp 896–899

Kamalesh Debnath, Sudipta Pathak, Animesh Pramanik*

Rubimycinone A, a new anthraquinone from a terrestrial Streptomyces sp. pp 900–902

Ritesh Raju, Oleksandr Gromyko, Viktor Fedorenko, Jennifer Herrmann, Andriy Luzhetskyy, Rolf Müller*

728 Contents / Tetrahedron Letters 54 (2013) 719–737

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The synthesis and ambipolar charge transport properties of 1,2,3,4-tetrafluoropentacene pp 903–906

Ching-Ting Chien, Ta-Chung Chiang, Motonori Watanabe, Ting-Han Chao, Yuan Jay Chang, Yan-Duo Lin, Hung-Kai Lee,Ching-Yang Liu, Chih-Hsin Tu, Chia-Hsing Sun, Tahsin J. Chow*

F

O

- CO

120 oC F

F

F

F

F

FF

A practical method for the regeneration of Kaiser-oxime resin pp 907–908

Sebastian Lüttenberg, Frank Sondermann, Jürgen Scherkenbeck*

A red fluorescent ‘turn-on’ chemosensor for Hg2+ based on triphenylamine–triazines derivatives with aggregation-induced emission characteristics

pp 909–912

Hao Zhang, Yi Qu, Yuting Gao, Jianli Hua*, Jing Li, Bo Li

A new sensitive and selective red fluorescence ‘turn on’ chemosensor 1 for Hg2+ was developed by taking advantage of AIE feature of triphenylamine–triazines motif and the specific binding of thymine with Hg2+. Moreover, chemosensor 1 exhibited large two-photon absorption cross-section (3328 GM).

Total synthesis of (±)-cis-trikentrin B via intermolecular 6,7-indole aryne cycloaddition and Stille cross-coupling pp 913–917

Nalin Chandrasoma, Neil Brown, Allen Brassfield, Alok Nerurkar, Susana Suarez, Keith R. Buszek*

NTBS

Br

Br

Br (20 equiv)

PhMe, -78 °C to rt

72%

n-BuLi ( 2.0 equiv)

NTBS

Br

NH

Br5 steps SnBu3

Pd2(dba)3 (2.5 mol%)

AsPh3 (10 mol%), THFMW, 150 °C, 23 min

73%

NH

(±)-cis-Trikentrin B

Contents / Tetrahedron Letters 54 (2013) 719–737 729

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Comparison and systematic optimization of synthetic protocols for DOTA–hydrazide generation pp 918–920

Felix Fuge, Marek Weiler, Jessica Gätjens, Twan Lammers, Fabian Kiessling*

Synthesis of b-hydroxy-d-trichloromethyl-d-valerolactones by intramolecular samarium/ytterbiumdiiodide-mediated Reformatsky reaction

pp 921–924

Thies M. Schulze, Jörg Grunenberg, Stefan Schulz*

OHCl3C

OCl3C

O

Br

kinetic resolution

OO

Cl3C OHmain diastereomer

OCl3C O

O

Br

RacemateReformatsky

SmI2/YbI2

favoured

Schwartz reagent mediated synthesis of thiazolones and imidazolones from thiazolidine-2,4-diones andimidazolidine-2,4-diones

pp 925–928

Srinivasa Reddy Dandepally, Radouane Elgoummadi, Alfred L. Williams*

NR

XO

O

X = S, NH, NR

NR

XO

Cp2Zr(H)Cl

THF, rt, 1 h

12 examples

A novel reduction/elimination method of thiazolidine-2,4-dione and imidazolidine-2,4-dione derivatives using Schwartz reagent to synthesize numerousthiazolones and imidazolones in a single step is reported.

A convenient procedure for N-formylation of amines pp 929–931

Sony Joseph, Prasenjit Das, Bindu Srivastava, Hashim Nizar*, Mohan Prasad

Formamide,NaOMe YOCNHCHO

R1THF

NHR

1

R2

Formamide,NaOMeN CHO

R1

R2

R2

OOCNH2

R1

R1= Alkyl, Aryl

R2= H, Alkyl

Y= OH, NH2

730 Contents / Tetrahedron Letters 54 (2013) 719–737

Page 13: Graphical contents list

Diastereoselective formation of b-hydroxyketones by the reduction of Ketene dimers pp 932–935

Pei-Hsun Wei, Melanie A. Gary, Divya Nalla, Gero D. Harzmann, Ahmad A. Ibrahim, Kyle R. Dayak, Nessan J. Kerrigan*

OO

R1

R2R2

R1

OH OR1

R2R1 R2

Reducing Agent

dr up to >99:1yield 62->99%

A general method for the diastereoselective formation of b-hydroxyketones by the reduction of ketene dimers was developed. Methylphenylketene dimerwas reduced with optimal diastereoselectivity (dr up to 6:1) using LiBH4. However, more generally LiAlH4 was found to be the most effective reducingsystem with respect to diastereoselectivity (dr up to >99:1) and yield (62–>99% for 10 examples).

The use of aqueous potassium dichloroiodate for the synthesis of ureas pp 936–940

Gil Mendes Viana, Lúcia Cruz de Sequeira Aguiar*, Jonas de Araújo Ferrão, Alessandro Bolis Costa Simas,Marcela Guariento Vasconcelos

NH

S

NHR1

NH

S

NHR1

or

NH

O

NHR1 KICl2 aq.CH3CN

or

NH

O

NHR1

NH

O

NHR1

I

method A method B(rt, 30 min) (reflux,1.5 h)

73-99%

KICl2 aq.CH3CN

77-99%

Synthesis of m-carboranyl amides via palladium-catalyzed carbonylation pp 941–944

Kiran Babu Gona, Vanessa Gómez-Vallejo, Jordi Llop*

NR1

O

R2

I

+

Pd catalystLigand

BaseCO, Pressure

NR2 R1

H

One-pot one-step reaction for the synthesis of secondary and tertiary m-carboranyl amides via palladium catalyzed carbonylation.

Biocatalytic asymmetric aldol reaction in buffer solution pp 945–948

Zong-Bo Xie, Na Wang*, Guo-Fang Jiang, Xiao-Qi Yu*

R1 H

O+ R3

R2

O

Acid buffer, 30oC R1

OH

R3

R2

OLipase

17 examples

Contents / Tetrahedron Letters 54 (2013) 719–737 731

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Efficient synthesis of bulky 4-substituted-isatins via microwave-promoted Suzuki cross-coupling reaction pp 949–955

Yu-Chao Liu, Chen-Jin Ye, Qiong Chen*, Guang-Fu Yang*

NH

O

O

I

+NH

O

O

R'Pd(PPh3)4 (5 mol%)

1. R = H2. R = CH3

3

NaHCO3 (2eq)DME/H2O = 5:1 (v/v)MW(130°C), 4~12min

ArB(OH)2

R = CH3, HR' = Ar, alkenyl

R Ror

alkenyl boronic acids

39 examplesYields : 45%~95%

Mechanistic aspect of ring transformations in the reaction of 5-nitro-4-pyrimidinone with acetophenonederivatives and cycloalkanones depending on the electron density/ring size of the ketone

pp 956–959

Nagatoshi Nishiwaki*, Ryuichi Sugimoto, Kazuhiko Saigo, Kazuya Kobiro

N

NO2N

MeO

NH4OAc

N

N

NH

NO2

O

+ (CH2)n(CH2)nO

(CH2)n

NH4OAc

n = 5 n = 4, 6

Site-selective mono-oxidative addition of active zinc into carbon–bromine bond of dibrominated-thiophenes:preparation of thienylzinc reagents and their applications

pp 960–964

Hye-Soo Jung, Hyun-Hee Cho, Seung-Hoi Kim*

S BrZn*

THF

rtS ZnBr

E+

S E'+

X X X

X: 3-Br, 5-Br

Condensation of propargylic alcohols with N-methylcarbazole and carbazole in [bmim]PF6 ionic liquid; synthesis ofnovel dipropargylic carbazoles using TfOH or Bi(NO3)3Æ5H2O as catalyst

pp 965–969

G. G. K. S. Narayana Kumar, Kenneth K. Laali*

10 mol% TfOHR1

OH

R2

R = MeR1, R3= ArylR2 = PhR4 = Ph, C4H9

(bmim)PF6

N

R1

R2

R1

R2

r.t.4-6 h

65-93%

N+

R

R

20 mol% Bi(NO3)3.5H2O(bmim)PF6

70 oC16-20 h49-66%

N

R3

R4

R1

R2

R

R3

OH

R4

R = H, MeR1 = ArylR2 = Ph, C4H9

732 Contents / Tetrahedron Letters 54 (2013) 719–737

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Terminal functionalization of atactic polypropylene: a new soluble polymer support pp 970–974

Binhong Lin, Devin Lawler, Gregory P. McGovern, Christopher A. Bradley, Christopher E. Hobbs*

An efficient transformation of ethers to N,N0-disubstituted ureas in a Ritter type reaction pp 975–979

Veladi Panduranga, Basavaprabhu, Vommina V. Sureshbabu*

NHCN

HN

HN

OR3

R1

R2R1

R2

R3

+BF3.Et2O (30 mol%)

AcOH, 40-50 oCO

O

HN

HN

OR3

R1

R2

HN

HN

OR3

R1

R2

O

RR

R

Enantioselective total synthesis of ())-ericanone pp 980–982

Luiz C. Dias*, Paula K. Kuroishi, Ellen C. Polo, Emílio C. de Lucca Jr.

O

HO OH

OH OH

rel-(3R,7R)-1structure proposedby Chulia's group

O

HO OH

OH OH

(3S,7S)-1structure assigned

in this work

3 73 7

Iron(III) tosylate catalyzed synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones via the Biginelli reaction pp 983–985

Jacob T. Starcevich, Thomas J. Laughlin, Ram S. Mohan*

Contents / Tetrahedron Letters 54 (2013) 719–737 733

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A facile synthesis of annulated azolo[c][1,2,4]thiadiazine S,S-dioxides pp 986–988

Artem Cherepakha*, Vladimir O. Kovtunenko, Andrey Tolmachev

R

Hal

S

O

Cl

X YN

HNH2N

+

N

NHS

N Y

X

R

OO

Hal = F or Br X,Y = CH,CR or N

O

Bioactive cembranoids from the Red Sea soft coral Sarcophyton glaucum pp 989–992

Rania F. Abou El-Ezz, Safwat A. Ahmed, Mohamed M. Radwan, Nahla A. Ayoub, Manal S. Afifi, Samir A. Ross,Pawel T. Szymanski, Hesham Fahmy, Sherief I. Khalifa*

OO

2

HO

O

HO

3

HO

6

1

4

6

8

11

12

15

20

18

16

HO

A ring-closing metathesis approach to heterocycle-fused azepines pp 993–997

Thomas A. Moss*

NR

Het HetN

R

Grubbs (II) 5 mol%CH2Cl2 or toluene

n n

20 examples5- and 6-memberedheterocyclesRT-70 oC

The pipecolic linker—an acid-labile handle for derivatization of secondary amines on a solid-support. Part 3 pp 998–1002

Paweł Zajdel*, Nicolas Masurier, Vittorio Canale, Pascal Verdie, Muriel Amblard, Maciej Pawłowski, Jean Martinez, Gilles Subra

734 Contents / Tetrahedron Letters 54 (2013) 719–737

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Graphite catalyzed green synthesis of quinoxalines pp 1003–1007

Hari K. Kadam, Salman Khan, Rupesh A. Kunkalkar, Santosh G. Tilve*

C

C

O

O

R1

R1

+NH2

NH2

R2 C

C

N

N

R1

R1

R2

GRAPHITE

Ethanol, r.t.

16 examples71 - 93 % isolated yield

Synthesis of substituted isatins pp 1008–1011

Larry L. Klein*, Michael D. Tufano

NH2

R2

R1

R2

R1

NH

O

O

NH

R2

R1

O

NOBn

isatins

H+HO2C NOBn

EDAC, HOBt

Isatins are valuable intermediates for heterocyclic chemistry. Most of the common methods for their production are less than adequate when the numberand lipophilicity of substituents on the targeted isatin are increased. Our group desired such molecules and identified an alternative method for theirproduction.

Total syntheses of (±)-folicanthine and (±)-chimonanthine via a double intramolecularcarbamoylketene–alkene [2+2] cycloaddition

pp 1012–1014

Takaaki Araki, Yuki Manabe, Kosuke Fujioka, Hiromasa Yokoe, Makoto Kanematsu, Masahiro Yoshida, Kozo Shishido*

Specific naked eye sensing of cyanide by chromogenic host: studies on the effect of solvents pp 1015–1019

Jongmin Kang*, Eun Joo Song, Hyun Kim, Young-Hee Kim, Youngmee Kim, Sung-Jin Kim, Cheal Kim*

NO2

NH

S

NN

NHost F- Cl- Br- I- CH3COO- CN- H2PO4

-

Contents / Tetrahedron Letters 54 (2013) 719–737 735

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trans-3-Hydroxy-4-morpholinopiperidine—the pH-triggered conformational switch with a double flip pp 1020–1024

Andrey V. Samoshin, Hyun Joo, Andrei Ya Korneichuk, Ivan S. Veselov, Galina V. Grishina, Vyacheslav V. Samoshin*

HN

OH -H+

H+

NOH

H

H

+N

N

-H+

H+ N

O

H N

H

H

++

H

δ-

δ-δ-

O O

O

Mono- and trifluorination of the thiazole ring of 2,5-diarylthiazoles using N-fluorobenzenesulfonimide (NFSI) pp 1025–1028

Julie M. Hatfield, Cheryl K. Eidell, Chad E. Stephens*

S

N

S

N

F

F

FNFSI (3 eq)

37%(no solvent)

S

N

F

NFSI (1 eq)Bromobenzene

155 °C135-140 °C

21%

A hydrozirconation/iodination-mediated access to tetrahydroquinolizinium salts. Application to the synthesis ofLupinine and ())-Epiquinamide

pp 1029–1031

Majdi Hajri, Clément Blondelle, Agathe Martinez, Jean-Luc Vasse*, Jan Szymoniak

N+

RI-

Cp2Zr(H)Cl

then I2

N

NAc

HH

N

R

N

OHH

(-)-Epiquinamide(±)-Lupinine

OTHER CONTENTS

Corrigendum to "Application of iron carbonyl complexation to the selective total synthesis of sanshools" [TetrahedronLett. 53 (2012) 6000-6003]

p 1032

736 Contents / Tetrahedron Letters 54 (2013) 719–737

Page 19: Graphical contents list

Corrigendum to ‘Synthesis of trifluoromethylated acetylenes via copper-catalyzed trifluoromethylation ofalkynyltrifluoroborates’ [Tetrahedron Lett. 53 (2012) 6646-6649]

p 1033

*Corresponding authorSupplementary data available via SciVerse ScienceDirect

Abstracted/indexed in: AGRICOLA, Beilstein, BIOSIS Previews, CAB Abstracts, Chemical Abstracts, Chemical Engineering andBiotechnology Abstracts, Current Biotechnology Abstracts, Current Contents: Life Sciences, Current Contents: Physical,Chemical and Earth Sciences, Current Contents Search, Derwent Drug File, Ei Compendex, EMBASE/Excerpta Medica, Medline,PASCAL, Research Alert, Science Citation Index, SciSearch. Also covered in the abstract and citation database SciVerse Scopus�.Full text available on SciVerse ScienceDirect�

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ISSN 0040-4039

Contents / Tetrahedron Letters 54 (2013) 719–737 737