Tetrahedron Letters Vol. 53, Issue 23, 2012

Contents

COMMUNICATIONS

The first report of [2+2] ketene–imine cycloaddition reactions (Staudinger) on carbon nanotubes pp 2797–2801

Aliasghar Jarrahpour*, Mohammad Mahdi Doroodmand, Edris Ebrahimi

O OH

O

TsCl, Et3N, CH2Cl2, rt

OAcO

AcO OAc N

AcO

X

Y

NO

O

X

Y

OOAc

OAcOAcOAc

Electrochemical selective oxidation of aromatic alcohols with sodium nitrate mediator in biphasic mediumat ambient temperature

pp 2802–2804

C. Christopher, S. Lawrence, M. Anbu Kulandainathan, K. Kulangiappar, M. Easu Raja, N. Xavier, S. Raja*

C / SS, aq.NaNO3 / CHCl3

ambient temperature R'R' R

O

R

OH

R = Phenyl, Substituted phenyl, benzyl, Ph-CH=CH-

R’ = H, alkyl Carbon anode(C) / (SS) Stainless Steel cathode

Catenane gel: synthesis of high molecular weight poly[2]catenanes by Sonogashira coupling polymerization pp 2805–2808

Toshiki Hagiwara*, Yasuhiro Murano, Yuki Watanabe, Toru Hoshi, Takashi Sawaguchi

NHNH

NH

NH

NH

O

O

O

O

IHN

HNNH

O

O

O

OI

Pd/CuSonogashira Coupling

NHNH

NH

NH

NH

O

O

O

O

HN

HNNH

O

O

O

O n

2787

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Enantioselective organocatalytic Michael addition of 2-arylacetates and 2-arylacetonitriles having anelectron-withdrawing group to a,b-unsaturated aldehydes

pp 2809–2812

Seung Woo Seo, Sung-Gon Kim*

+ Ar

O

HOMe

OEWG

up to 97% ee

EWG

OMeO

Ar

H

ONH

Ph

OTMS

Ph

(10 mol%)4-NO2C6H4CO2H

(10 mol%)

MeOH, rtEWG = NO2, CO2Me, CN

Toward the total synthesis of Luminamicin: construction of 14-membered lactone framework possessingversatile enol ether moiety

pp 2813–2816

Aoi Kimishima, Tomoyasu Hirose, Akihiro Sugawara, Takanori Matsumaru, Kaoru Nakamura, Ken Katsuyama,Masaki Toda, Hirokazu Takada, Rokuro Masuma, Satoshi �Omura*, Toshiaki Sunazuka*

1,3-Dipolar cycloaddition of a chiral nitrone to (E)-1,4-dichloro-2-butene: a new efficient synthesis of(2S,3S,4R)-4-hydroxyisoleucine

pp 2817–2821

Kaïss Aouadi*, Erwann Jeanneau, Moncef Msaddek, Jean-Pierre Praly*

NO

ON

ClH2C

H

CH2Cl

N

NO

O

H3C CO2H

OH

CH3

NH2(-)-1 (2S,3S,4R)-4-OH-Ile

21% overall yield

4 steps

ClH2CCH2Cl 1

2 3

45

70 %

Solvent dependency of the yield of an N-monosubstituted diaziridine: a GC–MS study pp 2822–2824

Peter Billing, Udo H. Brinker*

O NH21.) 3 h, rt, solvent2.) HOSA, 10 min.

NNH

NH2

2

SO42-+ +

2788 Contents / Tetrahedron Letters 53 (2012) 2787–2795

Copper-catalyzed cyanation of benzyl chlorides with non-toxic K4[Fe(CN)6] pp 2825–2827

Yunlai Ren, Chuanhua Dong, Shuang Zhao, Yanpei Sun, Jianji Wang*, Junying Ma, Chaodong Hou

K4[Fe(CN)6]+R

Cl

R

CNCuI

Copper-based catalysts were firstly introduced into the cyanation of benzyl chlorides with non-toxic K4[Fe(CN)6]. The presented method avoids theuse of extremely poisonous alkali cyanides and precious palladium catalysts. No other reagent apart from CuI, K4[Fe(CN)6] and toluene was used inthe cyanation, showing that the presented protocol is simple and practical. A series of benzyl chlorides were smoothly cyanated in up to 85% yieldunder the optimal conditions.

Sulfuric acid catalyzed addition of b-dicarbonyl compounds to alcohols under conventional heating andmicrowave-assisted conditions

pp 2828–2832

Fei Xia, Zheng Le Zhao, Pei Nian Liu*

R1 R2

O O+

R3 R4

OH 5 mol% H2SO4, CH3NO2R1 R2

O O

R4R3

15 examples;82-98% yields

101 oC, 5 min

Conventional heating

Microwave heatingSimilar results:

Stereoselective propargylation of glycals with allenyltributyltin(IV) via a Ferrier type reaction pp 2833–2836

Mark D. Drew, Mark C. Wall, Joseph T. Kim*

OO

O

OO

Si

SnBu3

OO

OSi

H+BF3·OEt2

DCM, RT

96%, α only

One-pot synthesis of unsymmetrical benzils from aryl methyl ketones and arenes in the presence ofselenous acid catalysed by p-toluenesulfonic acid monohydrate

pp 2837–2841

Icydora Kharkongor, Md. Rumum Rohman, Bekington Myrboh*

Het/ArO

H2SeO3

p-TsOH.H2O (30 mol%)Het/Ar

OAr'

O

Ar = aryl, Het = heteroaryl; Ar' = benzene, toluene, xylene,anisole, naphthalene, anthracene

H Ar'

Yields (54-75%)

Contents / Tetrahedron Letters 53 (2012) 2787–2795 2789

Halichoblelides B and C, potent cytotoxic macrolides from a Streptomyces species separated from a marine fish pp 2842–2846

Takeshi Yamada*, Takashi Kikuchi, Reiko Tanaka, Atsushi Numata

Substituted potassium internal vinyltrifluoroborates: preparation and use in Suzuki–Miyauracross-coupling reactions

pp 2847–2849

Shivanand K. Math*, Homayoun H. Mokri, James B. LaMunyon, Dustin R. Cefalo, Charles A. Testa

BrX

BF3KX

Pd(0)

Ar/HetArX

X=N,O

B(OR)3 Ar/HetArBr

An easy two step synthesis of macrocyclic peptidotriazoles via a four-component reaction and copper catalyzedintramolecular azide–alkyne [3+2] click cycloaddition

pp 2850–2855

D. Bahulayan*, S. Arun

+

HO

Cl

CH3OCH2Cl2

CuSO4, Stirr, rt.3h

O

CNBr

O

CuSO4.5H2O

O O

NNN

NH

+

NHO O OSodium ascorbate

DMSO-t-BuOH-H2O4:2:1

R.T.; 48h

+1.

2. NaN3, DMA, 3h, R.T. N3

O

K2CO3

Investigations on the synthesis of monoarylated diynes by monoprotection/cross-coupling/deprotection approach pp 2856–2859

Karolin Kral, Marko Hapke*

YZ

Y YZ

Y

SiMe3 Ar

YZ

Y1) Pd(PPh3)4, CuI,THF, NEt3, 55 °C2) KF, MeOH, rt

Y = CH2, SiMe2Z = O, CH2

LiHMDS,ClSiMe3,-78 °C - rt

+ disilylated byproduct

Ar I

2790 Contents / Tetrahedron Letters 53 (2012) 2787–2795

Cs2CO3 in pyrrolidinone promoted hydration of functionalized (hetero)aryl nitriles under metal-free conditions pp 2860–2863

Sophian Sahnoun, Samir Messaoudi*, Jean-François Peyrat, Jean-Daniel Brion, Mouad Alami*

Cs2CO3/Pyrrolidinone130 °C

2 h

15 examples61-99%

CNO

NH2

: Aryl, pyridine,furan, thiophene

(Hetero)aryl (Hetero)aryl

(Hetero)aryl

Various (hetero)aryl amides were efficiently prepared in good yields from the corresponding (hetero)aryl nitriles through addition of Cs2CO3 in pyrrolidinone.

Kanamycin A 60-pyrenylamide: a selective probe for heparin detection pp 2864–2867

Santosh V. Nalage, Sidhanath V. Bhosale*, Suresh K. Bhargava, Sheshanath V. Bhosale*

A novel derivative of kanamycin A bearing a pyrenyl fluorophore isdescribed and used for the specific recognition of heparin in EtOH:H2O(1:3) through formation of a 2:1 complex.

A novel scalable and stereospecific synthesis of 3a- and 3b-amino-5a-androstan-17-ones and 3a- and3b-amino-5a-pregnan-20-ones

pp 2868–2872

James R. Hitchin*, Niall M. Hamilton, Allan M. Jordan, Amanda J. Lyons, Donald J. Ogilvie

H2NH H

H

H H H2NH H

H

H H

OO

H

1 2 3 4

H2NH H

H

H H H2NH H

H

H H

OO

H

Kororamide A, a new tribrominated indole alkaloid from the Australian bryozoan Amathia tortuosa pp 2873–2875

Anthony R. Carroll*, Seanan J. Wild, Sandra Duffy, Vicky M. Avery

N

NCH3

O

N+CH3

H

Br

Br

CH3

Br N

NCH3

O

Br

Br

CH3

Br

N+

CH3

HH H

Contents / Tetrahedron Letters 53 (2012) 2787–2795 2791

Novel diversely substituted 1-heteroaryl-2-imidazolines for fragment-based drug discovery pp 2876–2880

Mikhail Krasavin*

N

N

N

Br

Pd-catalyzed93%

NN N N

NO

O

NH

N

O O

NH

N

O

NBr Br

+ 19 other examples(54 - 93%)

Pd-catalyzed79%

n-Butylammonium carboxylates/Tf2O: ionic liquid based systems for the synthesis of unsymmetrical imidesvia a Ritter-type reaction

pp 2881–2884

Mohammad Mehdi Khodaei*, Ehsan Nazari

RN

NH3 O R'

O+

60 °C, neat, 1 h R NH

R'

O O

R = Methyl, Aryl, BenzylR' = Methyl, n-Propyl, Isobutyl

Tf2O

Acremolin, a new 1H-azirine metabolite from the marine-derived fungus Acremonium strictum pp 2885–2886

Elin Julianti, Hana Oh, Hyi-Seung Lee, Dong-Chan Oh, Ki-Bong Oh*, Jongheon Shin*

N

NN

NH

O

N

Catalyst-free aza-Michael addition of azole to b,c-unsaturated-a-keto ester: an efficient access to C–N bondformation

pp 2887–2889

Jun Wang, Peng-Fei Li*, Sau Hing Chan, Albert S. C. Chan, Fuk Yee Kwong*

CO2R2

O

R1 + NN

R3

CO2R2

O

R1

NN

R3

CH2Cl2RT, 24 h

H

Aza-Michael Addition

(22 examples)

2792 Contents / Tetrahedron Letters 53 (2012) 2787–2795

Bromodimethylsulfonium bromide (BDMS)-mediated Lossen rearrangement: synthesis of unsymmetrical ureas pp 2890–2893

Deepak K. Yadav, Arvind K. Yadav, Vishnu P. Srivastava, Geeta Watal, Lal Dhar S. Yadav*

R1 NH

OH

O1.

2.

64-89%

, NMM

S

Br

Br

BDMS

DCE, 0 to 80 ºC

HNR2

R3

HN N

O

R1

, 7-18 h

R3

R2

An efficient total synthesis of calothrixin B pp 2894–2896

Shrikar M. Bhosale, Rupesh L. Gawade, Vedavati G. Puranik, Radhika S. Kusurkar*

N

OCH2PhCHO

N

OMe

OMePh

OH

PhBr

NaOCH3in CH3OH,

CuI, DMF,120oC, 10 hrs

NH

O

O

N

Calothrixin B

Polyethylene glycol (PEG-400): an efficient and recyclable reaction medium for the synthesis ofpyrazolo[3,4-b]quinoline derivatives

pp 2897–2903

K. Karnakar, S. Narayana Murthy, K. Ramesh, G. Satish, Jagadeesh Babu Nanubolu, Y. V. D. Nageswar*

NNPh

H3C

NH2

O

OR1

R1+ + PEG-400

100-110ºCR-CHO

R= Aryl, Hetero arylR1= H, CH3

N

R O

R1

R1N

NPh

H3C

DDQ-mediated direct oxidative coupling of amides with benzylic and allylic sp3 C–H bonds under metal-freeconditions

pp 2904–2908

D. Ramesh, U. Ramulu, K. Mukkanti, Y. Venkateswarlu*

R1 NH2

HN

R2Ar

R1

HNR1

DDQ, CH3NO2

DDQ, CH3NO2

n

Ar R2

n n = 1, 2

R1 = C6H5CO, PhCH2OCO, 4-CH3C6H4SO2,4-BrC6H4SO2, 4-CH3OC6H4SO2

Ph Ph , Ph CH3 ,

,

Ar R2 =

Contents / Tetrahedron Letters 53 (2012) 2787–2795 2793

LL-Proline catalyzed efficient one-pot three-component aza-Diels–Alder reactions on nitrostyrylisoxazoles: a facilesynthesis of new isoxazolyl tetrahydroquinolines and isoxazolo[2,3-a]pyrimidines

pp 2909–2913

E. Rajanarendar*, M. Nagi Reddy, K. Govardhan Reddy, S. Rama Krishna

4

HN

ArH HO

N

O2N

Ar'

CH3

HN

ArH HO

N

O2N

Ar'

CH3

5

N

N

ArH

Ar'

ON

O2N CH3

H

OH3C

N

N

ArH

Ar

ON

O CH3

H

OH3C

7 8

RR

LL-Proline acts as an efficient organo catalyst and found to promote one-pot three-component aza-Diels–Alder reaction of aryl or isoxazole imines formed in situ from aromatic orisoxazole amines and aromatic aldehydes with nitrostyrylisoxazoles to afford the isoxazolyl tetrahydroquinolines or isoxazolo[2,3-a]pyrimidines, respectively, in excellent yieldsat ambient temperature under neutral conditions.

Unexpectedly ligand-free copper-catalyzed C–S cross-coupling of benzothiazole with aryl iodides in aqueoussolution

pp 2914–2917

Yi-Si Feng, Hong-Xia Qi, Wei-Cheng Wang, Yu-Feng Liang, Hua-Jian Xu*

N

S+

I

NH2

SR

R

CuCl (5 mol%)nBu4NOH (40% aq., 1mL)

rt or 50 °C, Ar, 12 h

21 examplesyields: 79~99%

Highly selective fluorescent calix[4]arene chemosensor for acidic amino acids in pure aqueous media pp 2918–2921

Shao-Yong Li, Yao-Wei Xu, She-Quan Zeng, Li-Min Xiao, Hong-Quan Duan, Xue-Lian Lin, Jun-Min Liu*, Cheng-Yong Su*

Efficient syntheses of the versatile phthalide building blocks, 5,6-diaminoisobenzofuran-1(3H)-one and5H,7H-furo[3,4-f][2,1,3]benzothiadiazol-5-one

pp 2922–2924

Balázs Molnár, Gyula Simig, Tibor Bakó, András Dancsó, Balázs Volk*

O

O

ClO

NS

NO

O

O

NH2

NH2

NH

NH

CH2

O

3 steps

64% 83%

***potential transformations

2794 Contents / Tetrahedron Letters 53 (2012) 2787–2795

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ISSN 0040-4039

Contents / Tetrahedron Letters 53 (2012) 2787–2795 2795