Tetrahedron Letters Vol. 54, Issue 30, 2013

Contents

COMMUNICATIONS

Enantioselective Grignard addition to nitroolefin pp 3911–3915

Prashanth Reddy, Rakeshwar Bandichhor*

R1 NO2 NO2

R26 mol% L3

1.2 eq of R2MgXMTBE, 3 h

R1

5 mol% Cu(I)

upto 97% ee

Diastereoselective formation of 2,3,4,5-tetrasubstituted tetrahydrofurans by a Lewis acid promoted addition ofC3-substituted 1,3-bis(silyl)propenes to aldehydes

pp 3916–3918

Tessie Borg, Brian Timmer, Peter Somfai*

Synthesis of vinyliodides: progress toward the total synthesis of a jatrophane diterpene pp 3919–3925

Priya Mohan*, Michael J. Fuertes

HO

O

HO

1112

RCM

MOMO

O

MOMO

76

MOMOOMOM

+

4

5

7

I

H

O

metal-halide exchange or, NHK-coupling

3903

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A comparison of N- versus O-alkylation of substituted 2-pyridones under Mitsunobu conditions pp 3926–3928

Matthew C. Torhan, Norton P. Peet, John D. Williams*

N

OO

OEtN

O

OEt

R3

R5 R5

R3

+

1 2 3

O

NHR5

R3

O Mitsunobu

conditions

Ethyl lactate as a promising bio based green solvent for the synthesis of spiro-oxindole derivatives via1,3-dipolar cycloaddition reaction

pp 3929–3932

Anshu Dandia*, Anuj K. Jain, Ashok K. Laxkar

A novel anthracene-appended triazolium for fluorescent sensing to H2PO�4 pp 3933–3936

Qian-Yong Cao*, Zi-Chen Wang, Ming Li, Jing-Hua Liu

Zn(CF3SO3)2—mediated domino hydroamination-ring cleavage of 2,5-dihydrofuran pp 3937–3939

Xiao-juan Shen, Hong-zhong Bu, Jie Shi, Zheng-guang Wu, Hong-fei Ma, Yu-feng Li*

O

HN N

OH

Zn(CF3SO3)2R1

1 2 3

R1

tolueneR R+

3904 Contents / Tetrahedron Letters 54 (2013) 3903–3909

Synthesis of b-DD-GalNAc(4,6-diS)(1–4)[a-LL-Fuc(2,4-diS)(1–3)]-b-DD-GlcA, a novel trisaccharide unit of chondroitinsulfate with a fucose branch

pp 3940–3943

Jun-ichi Tamura*, Haruna Tanaka, Ayumi Nakamura, Naoko Takeda

An unusual thiazolo[5,4-d]thiazole sensitizer for dye-sensitized solar cells pp 3944–3948

Lorenzo Zani*, Gianna Reginato, Alessandro Mordini, Massimo Calamante, Maurizio Peruzzini, Maurizio Taddei,Adalgisa Sinicropi, Maria Laura Parisi, Fabrizia Fabrizi de Biani, Riccardo Basosi, Alessandro Cavallaro, Mara Bruzzi

Design and synthesis of a nucleoside and a phosphonate analogue constructed on a branched-threo-tetrofuranoseskeleton

pp 3949–3952

Y. B. Kiran, Hideaki Wakamatsu, Yoshihiro Natori, Hiroki Takahata*, Yuichi Yoshimura*

O B

HO

OH

OO

OH

N

N

O

NH2

PO

HOHO

OPO

HOHO

OH

N

N

O

NH2

cidofovir

O N

OP

N

N

N

NH2

PMDTA

O

HOHO

Enaminone ligand-assisted homo- and cross-coupling of terminal alkynes under mild conditions pp 3953–3955

Yunyun Liu*, Chunping Wang, Xiaobo Wang, Jie-Ping Wan

Contents / Tetrahedron Letters 54 (2013) 3903–3909 3905

A new library of 4(3H)- and 4,40(3H,3H0)-quinazolinones and 2-(5-alkyl-1,2,4-oxadiazol-3-yl)quinazolin-4(3H)-oneobtained from diaminoglyoxime

pp 3956–3959

Abolghasem Moghimi*, Rahim Hosseinzadeh Khanmiri, Ismail Omrani, Ahmad Shaabani

NH2

NOHHONH2N

N

HNO

NH

N

O

N

HN

HON

H2NO

R1

N

HNNONR2

O

R1

A : anthranilic acid derivative, AcOH, reflux B: methyl 2-aminobenzoate, zAcOH, reflux

A B

AcOH

(R2CO)2O

Lactosamine from lactulose via the Heyns rearrangement: a practical protocol pp 3960–3961

Yulong Shan, Farah Oulaidi, Martina Lahmann*

OOHHO

HOOH

OO

HO

HO

OH

HO

OOH

HOAcHN

OHO

OHHO

HOOH

O

CuBr2 catalyzed bromination/oxidation of isochromans to benzaldehyde derivatives pp 3962–3964

Mei-Yan Zhou, Shan-Shan Kong, Ling-Qiong Zhang, Ming Zhao, Jin-Ao Duan, Zhen Ou-yang*, Min Wang*

O

CuBr2(1.2 equiv.)

CH3CN82 °CR1

R2

OR1

R2Br

H12 examplesup to 68% yield

The application of vinamidinium salts to the synthesis of 1,2,4-trisubstituted pyrroles pp 3965–3966

Stanton Q. Smith*, Sean T. Dudek, Shu-Hui He, Jarod A. Girod, Shane R. Nunes

(H3C)2N N(CH3)2

NN CN

+CH3CN, reflux

ClO4

RR

CH3

triethylamineNH

.HCl

3906 Contents / Tetrahedron Letters 54 (2013) 3903–3909

Two new furostanol glycosides from the fruits of Tribulus terrestris pp 3967–3970

Seong Su Hong, Yun-Hyeok Choi, Wonsik Jeong, Jin Gwan Kwon, Jin Kyu Kim, Changon Seo, Eun-Kyung Ahn,Hyun Hwa Lee, Han-Jik Ko, Dong-Wan Seo, Joa Sub Oh*

O

O

O

OO

OH

HOHO OH

H

HH H

H

1a = α-OH1b = β-OH

R

Synthesis of 1,8-dioxooctahydroxanthene C-nucleosides pp 3971–3973

Chinmoy Manna, Sintu Kumar Samanta, Sudip Kumar Ghosh*, Tanmaya Pathak*

O

OO

OR

CHOO

OMeOBn

OBn

CHOO

OO

OMeCHOO

OO

OMeMeO

CHOO

OMeOMe

OMe

OMe

CHO

O O

X XX XO

O(OR)n

CHO

O(OR)n

Su =

R = Me, Bn

X = HX = Me

steps or one -pot

1,8-dioxooctahydroxanthene C-nucleosides have been synthesized forthe first time by reacting pyranosyl/furanosyl sugar aldehydes and cyclic1,3-dicarbonyls

Furan ring opening–pyrrole ring closure. A simple route to 1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-3-ones pp 3974–3976

Igor V. Trushkov*, Tatyana A. Nevolina, Vitaly A. Shcherbinin, Lyudmila N. Sorotskaya, Alexander V. Butin*

O R1

NH2NR3

R2

O R4

HClON

NH2

R2

R3

OR4

R1

OAcOH

AcOH, rt NN R1

OR4R3

R2

refluxONH

2 stepsR1R2

R3

Molecular iodine catalyzed transfer hydrogenation: reduction of aldimines, ketimines, and a-imino esters pp 3977–3981

Prabhakar Bachu, Chen Zhu, Takahiko Akiyama*

N

R3R1

R2

I2 (5 or 10 mol%)

R1 = aryl, alkylR2 = aryl, R3 = H, CH3, CO2R

NH

OEt

O

EtO

O

N

R3R1

R2H

Contents / Tetrahedron Letters 54 (2013) 3903–3909 3907

Copper(II) chloride promoted transformation of amines into guanidines and asymmetrical N,N0-disubstitutedguanidines

pp 3982–3984

Brendan Kelly, Isabel Rozas*

RNH2 N

HNH

NBoc

R BocNH

NH

SBoc Boc

NEt3, CuCl22-13

1

Synthesis and characterization of organic dyes containing 2,7-disubstituted carbazole p-linker pp 3985–3989

A. Venkateswararao, K. R. Justin Thomas*, Chuan-Pei Lee, Kuo-Chuan Ho

Convergent synthesis of (+)-xestodecalactone A via a Pd-catalyzed a-arylation reaction pp 3990–3992

Dripta De Joarder, Michael P. Jennings*

O

OBr

OtBu

OOMe

MeO O

O

OtBu

OPd-catalyzedα-arylation

OH

HO O

O

O

Steps

(+)-xestodecalactone

A new and efficient method for the synthesis of a,a-dihaloketones by oxyhalogenation of alkynes using oxone®–KX(X = Cl, Br, or I)

pp 3993–3996

Sridhar Madabhushi*, Raveendra Jillella, Kishore Kumar Reddy Mallu, Kondal Reddy Godala, Venkata Sairam Vangipuram

R HOxone® -KX

2 X=Cl (79-98%)3 X=Br (77-99%)

R= alkyl, aryl

R

O

H

XX

Oxone® -KI

CH3CN-H2O (2:1)

-10 oC

R

O

H

IIR

HI

I45

CH3CN-H2O (2:1)r.t.

5-52%47-94%

1

3908 Contents / Tetrahedron Letters 54 (2013) 3903–3909

[2+2] Photodimerization of bispyridylethylenes by a controlled shift of the protonation equilibrium pp 3997–4000

Shinji Yamada*, Momoko Kusafuka, Mai Sugawara

A NBD-based selective colorimetric and fluorescent chemosensor for Hg2+ pp 4001–4005

Jin Hoon Kim, Jin Young Noh, In Hong Hwang, Jae Jun Lee, Cheal Kim*

*Corresponding authorSupplementary data available via SciVerse ScienceDirect

COVER

Diastereoselective formation of 2,3,4,5-tetrasubstituted tetrahydrofurans by a Lewis acid promoted addition of C3-substituted1,3-bis(silyl)propenes to aldehydesTetrahedron Letters 2013, 54, 3916–3918.� 2013 Elsevier Ltd. All rights reserved.

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ISSN 0040-4039

Contents / Tetrahedron Letters 54 (2013) 3903–3909 3909