Tetrahedron 70 (2014) 4979e4990

Contents lists available at ScienceDirect

Tetrahedron
journal homepage: www.elsevier.com/locate/tet

Tetrahedron Vol. 70, Issue 34, 2014

Contents

REPORT
Recent developments in the synthesis and reactivity of methylene- and alkylidenecyclopropane derivatives

le
ne Pellissier
He

pp 4991e5031

This review collects the recent developments in the synthesis and reactivity of methylene- and alkylidenecyclopropane derivatives, covering the literature since
the beginning of 2010. Methylene- and alkylidenecyclopropanes are highly strained but remarkably stable and readily accessible molecules. Because of this
strained nature, associated with a large structural differentiation available, methylene- and alkylidenecyclopropanes show remarkable reactivities. This review
demonstrates that the chemistry of these compounds is the most rapidly developing among all small-ring compounds.

ARTICLES
Iron-catalyzed decarboxylative methylation of a,b-unsaturated acids under ligand-free conditions
Guangwei Rong, Defu Liu, Linhua Lu, Hong Yan, Yang Zheng, Jie Chen, Jincheng Mao*

R1

COOH
R2

FeCl3, DTBP

R1

DMSO, Ar

CH3
R2

CO2

pp 5033e5037

4980

Contents / Tetrahedron 70 (2014) 4979e4990

Synthesis of multi-functional alkenes via Wittig reaction with a new-type of phosphorus ylides
Yi-Ling Tsai, Siang-en Syu, Shu-Mei Yang, Utpal Das, Yu-Shiou Fan, Chia-Jui Lee, Wenwei Lin*

pp 5038e5045

An efcient synthesis of multi-functional alkenes has been described starting from commercially available starting materials.
Phosphorus ylide is the key intermediate in this approach. A plausible mechanism has been proposed and the products were
further converted to pyridazinone derivatives.

Synthesis and properties of a graphene-like macrocycle based on tetraphenylethene

Han Wang, Tingting Lin, Ji Ma, Weizhi Wang*

pp 5046e5051

Tandem Michael addition of amines to maleic anhydride and 1,3-prototropic shift: experimental and theoretical results
Asha Gurjar, Pragya Sinha, Raj K. Bansal*

pp 5052e5056

R1R2NH +

O
O

H O
H
O
R1R2NH
O

H O
H
O
R1R2N
OH

Synthesis of (S)-2-amino-7-methoxytetralin and isoindolo[1,2-a]isoquinolinone derivatives from L-aspartic acid

Jon Erik Aaseng, Odd R. Gautun*

pp 5057e5063

Contents / Tetrahedron 70 (2014) 4979e4990

Design, synthesis, photochromism and electrochemistry of a novel material with pendant photochromic units
Melek Pamuk Algi, Atilla Cihaner*, Fatih Algi*

4981

pp 5064e5072

A convenient preparation of (S)-(
)-4-hydroxy-2-methylcyclopent-2-en-1-one and its application as a chiral synthetic

equivalent of 2-methylcyclopent-2-en-1-one in the terpenoid synthesis
Karol Michalak, Jerzy Wicha*

pp 5073e5081

Studies on the synthesis of orthogonally protected azalanthionines, and of routes towards b-methyl azalanthionines,
by ring opening of N-activated aziridine-2-carboxylates

Proinsias, Fintan Kelleher*
Keith OBrien, Keith o

pp 5082e5092

TsHN

MeO2C

CO2All

PMB NHpNz

Orthogonally protected Azalanthionine

Iron-catalyzed benzamide formation. Application to the synthesis of moclobemide

de

ric Lamaty*
Xavier Bantreil*, Nasreddine Kanfar, Nicolas Gehin, Ethan Golliard, Pauline Ohlmann, Jean Martinez, Fre

pp 5093e5099

4982

Contents / Tetrahedron 70 (2014) 4979e4990

Effect of alkoxy terminal chain length on mesomorphism of 1,6-disubstituted pyrene-based hexacatenar liquid crystals:
columnar phase control
Takuji Hirose*, Hiroaki Takai, Mizuki Watabe, Hiroyuki Minamikawa, Tatsuya Tachikawa, Koichi Kodama, Mikio Yasutake

pp 5100e5108

Synthesis and photophysical properties of phenyl-sulfanylated chlororophyll derivatives

Natsuki Takei, Misaki Morioka, Mari Yoshizato, Takuya Tanaka, Shin-ichi Sasaki, Satoshi Ito, Hitoshi Tamiaki*, Toru Oba*

pp 5109e5113

Ph

Ph

S
PhSH
AIBN

NH

Fluorescence
emission

NH
N

(i) HBr/AcOH
(ii) PhSH

HN

NH
O

weak emission

COOMe

Asymmetric domino aza-MichaeleMichael reaction of o-N-protected aminophenyl a,b-unsaturated ketones:

construction of chiral functionalized tetrahydroquinolines
Shinae Kim, Ki-Tae Kang, Sung-Gon Kim*

pp 5114e5121

Development of a uoride-responsive amide bond cleavage device that is potentially applicable to a traceable linker
Jun Yamamoto, Nami Maeda, Chiaki Komiya, Tomohiro Tanaka, Masaya Denda, Koji Ebisuno, Wataru Nomura,
Hirokazu Tamamura, Youichi Sato, Aiko Yamauchi, Akira Shigenaga*, Akira Otaka*

pp 5122e5127

Contents / Tetrahedron 70 (2014) 4979e4990

4983

Palladium-catalysed SuzukieMiyaura coupling reactions of Bromhexine and Ambroxol

Muhammad Sharif, Anahit Pews-Davtyan, Jan Lukas, Susann Pohlers, Arndt Rolfs*, Peter Langer, Matthias Beller*

pp 5128e5135

Intramolecular Larock indole synthesis for the preparation of tricyclic indoles and its application in the synthesis
of tetrahydropyrroloquinoline and fargesine
Yan Gao, Dong Shan, Yanxing Jia*

pp 5136e5141

Synthesis and thermal properties of a new styryl-functionalized pentafulvene glassy carbon precursor
Endrit Shurdha, Hannah A. Miller, Russell E. Johnson, Gary J. Balaich*, Scott T. Iacono*

pp 5142e5147

Polyketide anthraquinone, diphenyl ether, and xanthone derivatives from the soil fungus Penicillium sp. PSU-RSPG99
Vatcharin Rukachaisirikul*, Siwaporn Satpradit, Saranyoo Klaiklay, Souwalak Phongpaichit,
Kawitsara Borwornwiriyapan, Jariya Sakayaroj

pp 5148e5152

4984

Contents / Tetrahedron 70 (2014) 4979e4990

Substituted benzoquinazolinones. Part 1: Synthesis of 6-aminobenzo[h]quinazolinones via BuchwaldeHartwig

amination from 6-bromobenzo[h]quinazolinones


zwiak, Emilia Fornal, Alina B1aszczyk, Renata Kontek
Monika Nowak*, Zbigniew Malinowski*, Andrzej Jo

pp 5153e5160

Synthesis of chromeno[3,4-c][1,2]oxazine-N-oxides via formal [4D2] cycloaddition of 3-nitro-2-trihalomethyl-2Hchromenes with cyclohexanone and pinacolone enamines
Vladislav Yu. Korotaev, Alexey Yu. Barkov, Evgeniya G. Matochkina, Mikhail I. Kodess, Vyacheslav Ya. Sosnovskikh*

pp 5161e5167

O
But
R

N
O
+
N
O

H
O

R
O

CX3

CCl3

H
O

CX3

R = H, MeO, Br, NO2;

X = Cl, F

But
NO2

NO2

CCl3

N
O
+
N

O
NO2
CCl3

From 4,5,6,7-tetrahydroindoles to 3- or 5-(4,5,6,7-tetrahydroindol-2-yl)isoxazoles in two steps: a regioselective switch

between 3- and 5-isomers
Lyubov N. Sobenina, Denis N. Tomilin, Maxim D. Gotsko, Igor A. Ushakov, Albina I. Mikhaleva, Boris A. Tromov*

pp 5168e5174

Stereospecic synthesis of highly substituted novel carbasugar as carbonic anhydrase inhibitors:

decahydronaphthalene-1,2,3,4,5,6,7-heptol
Latif Kelebekli*, Neslihan Balc, Ertan Sahin

pp 5175e5181

OH
H

HO

HO
OAc

OH

OH

OH
OH

Contents / Tetrahedron 70 (2014) 4979e4990

4985

Studies on bis(10 -ortho-carboranyl)benzenes and bis(10 -ortho-carboranyl)biphenyls

s E. Goeta, Judith A.K. Howard,
Rachel A. Harder, J.A. Hugh MacBride, Graham P. Rivers, Dmitry S. Yut, Andre
Ken Wade, Mark A. Fox*

pp 5182e5189

Improved synthesis of a functionalized 2,8-ethanonoradamantane derivative

mez, Ane Otermin
Pelayo Camps*, T
ania Go

pp 5190e5196

Synthesis of enantiopure free and N-benzyloxycarbonyl-protected 3-substituted homotaurines from naturally

occurring amino acids
Yongpeng Zheng, Jiaxi Xu*

pp 5197e5206

CbzHN

R
CO2H

CbzHN
7 examples

SO 3H

H2N

SO3H

3 examples

Iron uoride: the most efcient catalyst for one-pot synthesis of 4H-pyrimido[2,1-b]benzothiazoles under solvent-free
conditions
Amol B. Atar, Yong Seok Jeong, Yeon Tae Jeong*

pp 5207e5213

4986

Contents / Tetrahedron 70 (2014) 4979e4990

Synthesis of 3-carbonyl pyrazole-5-phosphonates via 1,3-dipolar cycloaddition of BestmanneOhira reagent with ynones
Mukund M.D. Pramanik, Ruchir Kant, Namrata Rastogi*

pp 5214e5220

O
R

O
O
HN
MeO
MeO

OMe

Me
KOH (1 eq)

R
O

R = aryl
2 examples; 79-81% yield

O
OMe
P
OMe
N

KOH (1 eq)

MeOH

MeOH

rt, 10 min

rt, 10 min

O OMe
P OMe

R = alkyl/aryl
R = aryl/TMS

NH

R = alkyl/aryl
R = aryl/H
17 examples; 79-90% yield

Molecular iodine catalyst promoted synthesis of chromans and 4-aryl-3,4-dihydrobenzopyran-2-ones via [3D3]
cyclocoupling
Mayuri M. Naik, Durga P. Kamat, Santosh G. Tilve*, Vijayendra P. Kamat

pp 5221e5233

Synthesis of a chiral phosphonium salt for the preparation of a-substituted alaninol derivatives
Takashi Tsuji*, Keisuke Suzuki, Tsuyoshi Nakamura, Takahide Nishi

pp 5234e5241

Access to fused pyrroles via the reaction of spiro-dienyl ethers with amines involving a chemoselective skeletal
rearrangement
Xiaoyu Zhang, Li Huang, Hui Peng, Fanghua Ji, Xuehui Li, Biaolin Yin*

pp 5242e5248

R1

R1
known method
Ar

NR

O
OH

Ar

NEt

R2NH2
O
6

NEt p-TsOH (20 mol %) Ar

DCE, 105 oC, 16 h

N
R2

11

R1

26 examples
yields up to 83%

Contents / Tetrahedron 70 (2014) 4979e4990

4987

PdeCo bimetallic nanoparticles supported on graphene as a highly active catalyst for SuzukieMiyaura and Sonogashira
cross-coupling reactions
Yi-Si Feng, Xin-Yan Lin, Jian Hao, Hua-Jian Xu*

pp 5249e5253

Synthesis of calix[4]arene-based polycarboxylate ligands and their chemical immobilization onto controlled-pore glass
Sebastian Haupt, Marcel Handke, Robert Kuhnert, Maria Poetsch, Berthold Kersting*

pp 5254e5259

Sulfation of deoxynivalenol, its acetylated derivatives, and T2-toxin

Philipp Fruhmann*, Philipp Skrinjar, Julia Weber, Hannes Mikula, Benedikt Warth, Michael Sulyok, Rudolf Krska,
hlich
Gerhard Adam, Erwin Rosenberg, Christian Hametner, Johannes Fro

pp 5260e5266

A mild and efcient AgSbF6-catalyzed synthesis of fully substituted pyrroles through a sequential
propargylation/amination/cycloisomerization reaction
Satheesh Gujarathi, Xingui Liu, Lin Song, Howard Hendrickson, Guangrong Zheng*

pp 5267e5273

4988

Contents / Tetrahedron 70 (2014) 4979e4990

CuO nanoparticles catalyzed simple and efcient synthesis of 2,3-dihydroquinazolin-4(1H)-ones and quinazolin-4(3H)ones under ultrasound irradiation in aqueous ethanol under ultrasound irradiation in aqueous ethanol
Jin Zhang*, Decheng Ren, Yangmin Ma*, Weitao Wang, Hao Wu

pp 5274e5282

Preparation of fused b-lactams through Weinreb amide a-anions

William M. Hewitt, Michael Egger, Nathaniel B. Zuckerman, Joseph P. Konopelski*

pp 5283e5290

Synthesis and evaluation of N6-substituted azide- and alkyne-bearing N-mustard analogs of S-adenosyl-L-methionine
Mohamed Ramadan, Natalie K. Bremner-Hay, Steig A. Carlson, Lindsay R. Comstock*

pp 5291e5297

Free-radical selective functionalization of 1,4-naphthoquinones by peruorodiacyl peroxides

Maurizio Sansotera*, Cristian Gambarotti, Antonino Famulari, Alberto Baggioli, Raffaella Soave, Francesco Venturini,
Stefano V. Meille, Ivan Wlassics, Walter Navarrini

pp 5298e5309

Contents / Tetrahedron 70 (2014) 4979e4990

4989

New synthetic methods for 2,3-diarylacridin-9(10H)-one and (E)-2-aryl-4-styrylfuro[3,2-c]quinoline derivatives

Vera L.M. Silva*, Artur M.S. Silva*

pp 5310e5320

Formation of 3-acyloxy-g-butyrolactones from 4-pentenols in vanadium-catalyzed oxidations

nges, Georg Stapf, Jens Hartung*
Matthias Amberg, Maike Do

pp 5321e5331

Highly syn selective addition of aqueous HBr to hydrophobically shielded arylalkynes

hrer
Rudolf Knorr*, Eva C. Rossmann, Monika Knittl, Petra Bo

pp 5332e5338

*Corresponding author
Supplementary data available via ScienceDirect

4990

Contents / Tetrahedron 70 (2014) 4979e4990

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