Tetrahedron Letters Vol. 54, Issue 40, 2013

Contents

COMMUNICATIONS

Synthesis, X-ray analysis and photophysical properties of a new N-containing pentacyclic helicene pp 5421–5425

Mourad Ben Braiek, Faouzi Aloui, Souad Moussa, Moncef Tounsi, Jérome Marrot, Béchir Ben Hassine*

A photolabile protection strategy for terminal alkynes pp 5426–5429

Tina A. Gschneidtner, Kasper Moth-Poulsen*

T3P�-promoted Kabachnik–Fields reaction: an efficient synthesis of a-aminophosphonates pp 5430–5433

Mátyás Milen, Péter Ábrányi-Balogh, András Dancsó, Dávid Frigyes, László Pongó, György Keglevich*

26°C, 5 minT3P

EtOAcAr1 CHO Ar2 NH2+ + P(OEt)3

HNAr2

Ar1 P(O)(OEt)280−96%

Ar1 = 4-MeC6H4, 4-FC6H4, 4-ClC6H4, 4-O2NC6H4, 4-F3CC6H4, 4-MeOC6H4, 4-BnOC6H4, 3-NCC6H4, 1-naphthylAr2 = Ph, 4-MeC6H4, 4-PhC6H4, 4-FC6H4, 4-ClC6H4, 4-BrC6H4, 4-O2NC6H4, 4-EtO2CC6H4, 4-MeOC6H4,

3,4-(MeO)2C6H3, 2-MeSC6H4, 2-Ph(OC)C6H4, 3-PhOC6H4, 3-F3CC6H4, 3-F3COC6H4, 1-naphthyl

5411

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Tetrahedron Letters

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

One pot four-component reaction for the efficient synthesis of spiro[indoline-3,40-pyrano[2,3-c]pyrazole]-30-carboxylate derivatives

pp 5434–5440

Suman Pal, Md. Nasim Khan, Shaik Karamthulla, Sk Jahir Abbas, Lokman H. Choudhury*

N

O

OCN

R3

PhHNNH2

COOR4R4OOC

R2

Et3N, EtOH,rt

O

R3

H2N NNH

NO

COOR4

R2

R1

R1

2C-C, 2C-N, 1C-O bond formation

H2NNH2.H2O

O

R3

H2N NN

NO COOR4

R2R1

Ph

Synthesis and dynamic study of new ortho-(alkylchalcogen)acetanilide atropisomers. A second lookat the hydrolysis of quaternary 2-methylbenzazol-3-ium salts

pp 5441–5444

Susana S. Ramos, Lucinda V. Reis, Renato E. F. Boto, Paulo F. Santos, Paulo Almeida*

Experimental temperature dependence of 1H NMR | Computer line shape simulation

I

X = O, S, Se; R = Et, Hex

N

XR

N

X

Studies on the synthesis and biosynthesis of the fungal alkaloid necatorone pp 5445–5447

Jörn Carstens, Markus R. Heinrich*, Wolfgang Steglich*

NO

CO2Me

N

3-aminotyrosine

NH2

HNHO

CO2H

CO2H

F

NH2

NH2

HO

CO2H

CO2Me

NH2

MeO

N

Cu-mediated 1,3-dipolar cycloaddition of azomethine ylides with dipolarophiles: a faster access to spirooxindolesof potential pharmacological interest

pp 5448–5452

Shambhu Nath Singh, Sridhar Regati, Abir Kumar Paul, Mohosin Layek, Sarva Jayaprakash, K. Venkateshwara Reddy,Girdhar Singh Deora, Soumita Mukherjee, Manojit Pal*

NH

O

OH

+N

O

O O R3N

NO

R3OC

R1

R1

R2

R2CuI

MeCN80-85 oC

12 examples; 75-92% yieldCu-mediated three-component reaction afforded novel spirooxindoles for the potential inhibition of PDE4.

5412 Contents / Tetrahedron Letters 54 (2013) 5411–5419

Highly regioselective hydroselenation of inactivated terminal alkynes using diselenide–Ph2P(O)H mixedsystems under visible-light irradiation

pp 5453–5456

Yohsuke Kobiki, Shin-ichi Kawaguchi, Akiya Ogawa*

R (R'Se)2Ph2P(O)H (3a)

+hν (>300 nm)

1 2 4

R SeR'

A cytotoxic dimeric furanoheliangolide from Piptocoma rufescens pp 5457–5460

Yulin Ren, Francisco Jiménez, Ricardo García, Milciades Mejía, Heebyung Chai, Norman R. Farnsworth, Djaja D. Soejarto,A. Douglas Kinghorn*

O

O

O

O

O

O O

O

O

O

O

O

1

A solvent-free amidation of vinylogous esters via direct aziridination pp 5461–5463

Emily C. McLaughlin*, Anuska Shrestha, Madison H. Fletcher, Nathaniel S. Steinauer, Min Kyung Shinn,Sabrina M. Shahid

Reductive iodonio-Claisen rearrangement of iodothiophene diacetates with allylsilanes: formal synthesis of Plavix� pp 5464–5466

Hai Nguyen, Hem Raj Khatri, Jianglong Zhu*

BF3 Et2O, CH2Cl2,-50°C, 2 h

Me3Si

S S

I

97% yield

I(OAc)2

S

N

Cl

CO2Me

Plavix

Contents / Tetrahedron Letters 54 (2013) 5411–5419 5413

Non-phosgene route to unsymmetrical ureas from N-Cbz-a-amino acid amides pp 5467–5469

Ebrahim H. Ghazvini Zadeh*, Nader E. Abo-Dya, Ania C. Sotuyo, Ion Ghiviriga, C. Dennis Hall

BnO

O

NH

R1

O

NHR2

O

NH

R1

OR2HN

RO-

1 2

OHN

R1

O

NR2

HO- RO-

Expanding the scope of the asymmetric anti-aldol addition of chiral N-amino cyclic carbamate hydrazones pp 5470–5472

John D. Knight, Don M. Coltart*

A novel reaction of the ‘Huisgen zwitterion’ with benzofuran-2,3-diones: an efficient strategy for the synthesis ofspirocyclic benzofuran-2-one derivatives

pp 5473–5476

Ze-Dong Wang, Nan Dong, Feng Wang, Xin Li*, Jin-Pei Cheng*

Environmentally benign deprotection of dithioacetals using 30% hydrogen peroxide catalyzedby Fe(acac)3 and sodium iodide

pp 5477–5480

Masayuki Kirihara*, Satoshi Suzuki, Yuki Ishizuka, Kento Yamazaki, Ryoji Matsushima, Takaya Suzuki, Toshiaki Iwai

R R'SS

R R'

OFe(acac)3 (0.1 eq.), NaI (1.0 eq.),30% H2O2 (4.0 eq.)

AcOEt-H2O = 1 : 1, r.t. 99~78%

R1

R3R4

O

O

NN

O

OR5O

+ NN

R5O2C

CO2R5O

R1

R3R4

O

O

CH2Cl2, rt, <10 min

R2R2PPh3

OR5

13 examplesup to 93% yield

5414 Contents / Tetrahedron Letters 54 (2013) 5411–5419

Armillariols A to C from the culture broth of Armillaria sp. pp 5481–5483

Hajime Kobori, Atsushi Sekiya, Nobuhiro Yasuda, Keiichi Noguchi, Tomohiro Suzuki, Jae-Hoon Choi, Hirofumi Hirai,Hirokazu Kawagishi*

Selectivity between N-1 and N-7 nucleosides: regioselective synthesis of BMK-Y101, a potent cdk7 and 9 inhibitor pp 5484–5488

Young-Jong Kim, Soon Ho Kwon, Il Hak Bae, B. Moon Kim*

Bidirectional synthesis of montamine analogs pp 5489–5491

Melanie B. Freitas, Kelly A. Simollardes, Caroline M. Rufo, Chantel N. McLellan, Gabrielle J. Dugas, Leslie E. Lupien,Elizabeth A. Colby Davie*

Regio- and stereoselective synthesis of (Z)-2-Arylsulfanyl allylic alcohols using anhydrous CeCl3 as catalystunder solvent free conditions

pp 5492–5495

Claudio C. Silveira*, Guilherme M. Martins, Samuel R. Mendes

H3CCH3

C2H5S S

CH3HO

H3C

HO

H3C CH3+ Solvent free, 80 °C

CeCl3 (20 mol%)MeNO2 (2 mL/mmol)

CeCl3 (20 mol%)

R-SH0.5 h, 81%3.0 h, 42%

Contents / Tetrahedron Letters 54 (2013) 5411–5419 5415

Palladium-catalyzed aminocarbonylation of aryl iodides using aqueous ammonia pp 5496–5499

Tongyu Xu, Howard Alper*

O O

O P

CH3

H3C

CH3

CH3

Ph

CYTOP® 292

I

+ NH3aqueous

+Pd(OAc)2/CYTOP® 292

CONH2

CO (100 psi )tolueneR R

One-pot solid phase synthesis of (E)-nitroalkenes pp 5500–5504

Lalthazuala Rokhum, Ghanashyam Bez*

R1

O

HR2 NO2+

R1

NO2

R2

CH2Cl2, RT

PPh2/I2/ImH

An efficient protocol for the synthesis of (E)-nitroalkene by sequential one-pot reaction of aldehyde and nitroalkane in the presence of polymer-boundtriphenylphosphine, iodine, and imidazole is described. One-step synthesis of nitroalkenes without using conventional dehydrating reagents, easypurification, and excellent yield of the products are some of the major advantages of the protocol.

DBSA mediated chemoselective synthesis of 2-substituted benzimidazoles in aqueous media pp 5505–5509

Vikash Kumar, Dipratn G. Khandare, Amrita Chatterjee*, Mainak Banerjee*

Microwave assisted efficient aminocarbonylation of N-tosylhydrazones with molybdenum hexacarbonyl and amines pp 5510–5513

K. Penta Rao, Ashok K. Basak, Amancha Raju, Vikas S. Patil, L. Krishnakanth Reddy*

23 examples, 44-82% yield

H2N+

R3Mo(CO) 6, Et4NCl

DBU, DioxaneMicrowave, 140 °C, 45 min

NNHTs

R2

R2

O

R3HN

R1 R1

5416 Contents / Tetrahedron Letters 54 (2013) 5411–5419

Synthesis and spectral properties of ruthenium(II) complexes based on 2,20-bipyridines modified by a perylenechromophore

pp 5514–5517

Koichi Kodama, Akinori Kobayashi, Takuji Hirose*

N

N

N N

N

N RuII

N N

O

O

O

O

R

π-conjugated perylene diimideperylene

Ru(II) + 2,2'-Bipyridine + Perylene chromophores

Synthesis of bifunctional cyclic carbonates from CO2 catalysed by choline-based systems pp 5518–5522

Adérito J. R. Amaral, Jorge F. J. Coelho, Arménio C. Serra*

Lipase from Carica papaya latex presents high enantioselectivity toward the resolution of prodrug (R,S)-2-bromophenylacetic acid octyl ester

pp 5523–5526

Ivanna Rivera, Juan Carlos Mateos, Alain Marty, Georgina Sandoval, Sophie Duquesne*

Pd(OAc)2-catalyzed oxidative carbonylation of aromatics: synthesis of naphthalenecarboxylic acids pp 5527–5531

Alexander R. Elman*

COOHO OO

+COPd(OAc)2,

K2S2O8

Contents / Tetrahedron Letters 54 (2013) 5411–5419 5417

A new route to the synthesis of isoxazoline derivatives from dihydropyran via cycloaddition reaction in ionic liquid pp 5532–5536

Bhaskar Chakraborty*, Chiran Devi SharmaRNHOH

NO H

R1 R2

RR3

12

3

45

[bmim]BF4

[bmim]BF4

R = CH3/C6H5/C6H11/ C6H5CH2/4-OHC6H4/2-OHC6H4

R1 = Ph ; R2 = COOCH3

R1 = R2 = COOCH3

R1 = R2 = COOHR3 = -(CH2)4OHR4 = H ; CH3 ; C6H5

R2R1

OO N

OH

R

OHN+

O-

R1

OHN+

O-

R1 2

C

H2N

R4COOH

H

N

OR1

C

R

H R3

N

O

H

C

HC

R4

O

HO

3

N

R

R1

O

R2

R3

2a

A new approach to the synthesis and 1,3-dipolar cycloadditions of nitrones has been described from 2,3-dihydro-4H-pyran and various hydroxylamines,with electron-deficient alkynes for the synthesis of isoxazoline derivatives. Significant rate acceleration and improved yields of exclusively exoisoxazolines in 1-butyl-3-methylimidazolium based ionic liquids have been observed. Novel isoxazolines may be used as a precursor for the synthesis ofvariety of peptides.

A one-pot, three-component, microwave-promoted synthesis of 2-amino-substituted 7-amino-1,2,4-triazolo[1,5-a][1,3,5]triazines

pp 5537–5540

Svetlana A. Kalinina, Dmitrii V. Kalinin, Anton V. Dolzhenko*

N

N

NN

NN

NH2

NHN

N NH2

NH2

HC(OEt)3

+

N

Nmicrowaves

R1

R2R2

R1

4-CF3-ezetimibe analogs: design, synthesis, and biological evaluation of cholesterol absorption inhibitions pp 5541–5543

Yingle Liu, Jun-Ling Chen, Gai-Hong Wang, Peng Sun, Heyao Huang, Feng-Ling Qing*

NO

F

OH

Ezetimibe

OH

FN

O

F

OH

F

CF3

1a

CF3

93% inhibitionof cholesterol absorpion

73% inhibitionof cholesterol absorpion

OTHER CONTENT

Corrigendum to ‘‘The Michael addition of 1,2-cyclohexanedione to b-nitrostyrenes (I): the synthesis of 3-aryl-5,6-dihydrobenzofuran-7(4H)-ones’’ [Tetrahedron Lett. 54 (2013) 3371–3373]

p 5544

Chad M. Simpkins, David A. Hunt*

5418 Contents / Tetrahedron Letters 54 (2013) 5411–5419

Corrigendum to ‘‘Surprising behavior of NXO-peptides toward the lithium hydroxide solvolysis’’[Tetrahedron Lett. 54 (2013) 3679–3682]

p 5545

Farhan A. Khan*, Constantin Rabong, Ulrich Jordis, Jaywant Phopase*

*Corresponding authorSupplementary data available via ScienceDirect

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Contents / Tetrahedron Letters 54 (2013) 5411–5419 5419