Tetrahedron 70 (2014) 2295e2301

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Tetrahedron

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

Tetrahedron Vol. 70, Issue 14, 2014

Contents

PREFACE

Tribute to Professor Yoshinori Yamamoto

pp 2303e2304 Stephen Martin, Kiyoshi Tomioka

PERSPECTIVES

Perspectives on organic synthesis using nanoporous metal skeleton catalysts

pp 2305e2317 Yoshinori Yamamoto

ARTICLES

Hydrazones fromhydroxy naphthaldehydes. Part 2. Condensations with aromaticN-aminoheterocycles and elucidationof tautomeric structures

pp 2319e2329

R. Fernando Martínez*, Martín �Avalos, Reyes Babiano, Pedro Cintas, Mark E. Light, Jos�e L. Jim�enez, Juan C. Palacios*

Contents / Tetrahedron 70 (2014) 2295e23012296

10-Acetylferrocene amino acid esters and amides. A simple model for parallel b-helical peptides

pp 2330e2342 Senka Djakovi�c, Ivan Kodrin, Vilko Smre�cki, Predrag Novak, Zlatko Mihali�c, Dinko �Ziher, Jasmina Lapi�c*,Vladimir Rapi�c

2-Substituted thiazole-4-carboxamide derivatives as tiazofurin mimics: synthesis and in vitro antitumour activity pp 2343e2350

Mirjana Popsavin*, Vesna Koji�c, Sa�sa Spai�c, Milo�s Svir�cev, Gordana Bogdanovi�c, Dimitar Jakimov, Lidija Aleksi�c,Velimir Popsavin

2-Substituted thiazole-4-carboxamides 2, 3, 4 and 16 have been synthesized and found to inhibit the growth of selected human tumour cell lines.It was shown that the antiproliferative effects of these molecules in the culture of K562 cells probably originate in caspase-dependent apoptosis.

A total synthesis of a highly N-methylated cyclodepsipeptide [2S,3S-Hmp]-aureobasidin L using solid-phase methods pp 2351e2358

Rani Maharani, Robert T.C. Brownlee, Andrew B. Hughes, Belinda M. Abbott*

Reactions of enaminones and related compounds with N,N-dimethylacetamide dimethyl acetal. A simple one-pot pp 2359e2369

metal-free synthesis of polysubstituted benzene derivatives Benjamin Prek, Jure Bezen�sek, Marta Kasuni�c, Uro�s Gro�selj, Jurij Svete, Branko Stanovnik*

Contents / Tetrahedron 70 (2014) 2295e2301 2297

Synthesis of a stable triformylmethane synthon and its scalable application to 7-acylamino-3-formylquinoline pp 2370e2377

syntheses Yasuhiro Sawai*, Masahiro Mizuno, Tatsuya Ito, Mitsuhisa Yamano

b-Biguanidinium-cyclodextrin: a supramolecular mimic of mitochondrial ADP/ATP carrier protein pp 2378e2382

Huo-Yan Chen, Meng Zhao, Jia-Heng Tan, Zhi-Shu Huang, Gao-Feng Liu, Liang-Nian Ji, Zong-Wan Mao*

Modified b-cyclodextrinwith a cationic biguanidyl group exhibits high binding affinity toward AMP, ADP, and ATP inwater, whichmimic the functionof mitochondria ADP/ATP carrier protein (AAC). The cationic biguanidyl group plays a role analogue to the Arg residues of mitochondrial AAC.

CuCl-catalyzed one-pot synthesis of 5,6-dihydropyrazolo[1,5-c]quinazolines pp 2383e2388

Shenghai Guo*, Jiliang Wang, Yan Li, Xuesen Fan*

Catenar bimetallomesogens derived from quinoxalineesalicylaldimine conjugates pp 2389e2399

Yian-Yuan Chu, Hsiu-Ming Kuo, Yu-Che Wu, Chin-Yi Wu, Hwo-Shuenn Sheu, Gene-Hsiang Lee, Ming-Chou Chen*,Chung K. Lai*

X = H, OR; M = Cu, Pd, Zn

N

N

OR1

OR1OR1

OR1

O

O

NO

X

ON

N

R1O

R1OR1O

R1O

O

O

NO

X

O MM

Contents / Tetrahedron 70 (2014) 2295e23012298

Transition-metal-free synthesis of multisubstituted N-arylindoles via reaction of arynes and a-amino ketones pp 2400e2405

Lin He*, Ji-Xin Pian, Jun-Feng Shi, Guang-Fen Du, Bin Dai

Synthesis of multisubstituted N-arylindoles via cycloaddition of arynes.

Asymmetric organocatalytic conjugate addition of dialkyl phosphites to N-unprotected isatylidene malononitriles: pp 2406e2415

access to 3-phospho-2-oxindoles with chiral quaternary stereocenters Zhao-Min Liu, Nai-Kai Li, Xiao-Fei Huang, Bing Wu, Ning Li, Chun-Yuen Kwok, Yong Wang*, Xing-Wang Wang*

Synthesis of 1,4-diarylsubstituted 1,3-diynes through ligand-free copper-catalyzed oxidative decarboxylative pp 2416e2421

homocoupling of aryl propiolic acids De-Xian Liu, Fei-Long Li, Hong-Xi Li*, Jun Gao, Jian-Ping Lang*

2,3-Diarylquinoxaline directed mono ortho-aroylation via cross-dehydrogenative coupling using aromatic pp 2422e2430

aldehydes or alkylbenzenes as aroyl surrogate Sourav Kumar Santra, Arghya Banerjee, Bhisma K. Patel*

Contents / Tetrahedron 70 (2014) 2295e2301 2299

Vanadium-catalyzed green oxidation of benzylic alcohols in water under air atmosphere pp 2431e2438

Kuniaki Marui, Yuuki Higashiura, Shintaro Kodama, Suguru Hashidate, Akihiro Nomoto, Shigenobu Yano,Michio Ueshima, Akiya Ogawa*

R1OH

R2 R1 R2O

VOSO4 (5 mol%), 4,4'-t-Bubpy (10 mol%)

H2O (0.5 mL)

O2 or Air (0.1 MPa)

N-Acetyl-5-arylidenetetramic acids: synthesis, X-ray structure elucidation and application to the preparation of zinc(II) pp 2439e2443

and copper(II) complexes Dimitris Matiadis*, Olga Igglessi-Markopoulou, Vickie McKee, John Markopoulos*

Scalable synthesis of (�)-trans-3-hydroxypipecolic acid via a useful chiral building block pp 2444e2448

Oskari K. Karjalainen, Ari M.P. Koskinen*

Aza-Michael reaction: selective mono- versus bis-addition under environmentally-friendly conditions pp 2449e2454

Giovanna Bosica*, Jonathan Spiteri, Caroline Borg

Contents / Tetrahedron 70 (2014) 2295e23012300

Stereoselective synthesis of CF3-substituted trans- and cis-enediynes via carbocupration or hydrostannation pp 2455e2463

reactions of CF3-containing diyne Tsutomu Konno*, Misato Kishi, Takashi Ishihara, Shigeyuki Yamada

F3C R1F3C

R2

R1

F3C H

R1R3 R3

trans-endiynes cis-endiynes

via Carbocupration

via Hydrostannation

Oxidation of disulfides with electrophilic halogenating reagents: concise methods for preparation of thiosulfonates pp 2464e2471

and sulfonyl halides Masayuki Kirihara*, Sayuri Naito, Yuki Nishimura, Yuki Ishizuka, Toshiaki Iwai, Haruka Takeuchi, Tomomi Ogata,Honoka Hanai, Yukari Kinoshita, Mari Kishida, Kento Yamazaki, Takuya Noguchi, Shiro Yamashoji

CH3CN-H2O, rt

2 R S FO

O

R S S RO

O

SelectfluorTM(2.5 eq.)

SelectfluorTM (6.5 eq.)

CH3CN-H2O, reflux

R S S RSelectfluorTM

(4.5 eq.)CH3CN-H2O, reflux2 R S Br

O

O

2 R S ClO

OCH3CN-H2O, rt

NCS (6.0 eq.)

NBS (6.0 eq.)

CH3CN-H2O, rt

An atom-economic synthesis of functionalized pyrroles via a sequential metal-catalyzed three-component reaction pp 2472e2477

Li Yufeng*, Shi Jie, Wu Zhengguang, Wang Xinglong, Wu Xiaowei, Gu Jiachao, Bu Hongzhong, Ma Hongfei

Influence of polyhedral oligomeric silsesquioxanes (POSS) on blue light-emitting materials for OLED pp 2478e2486

Tianfu Zhang, Jinze Wang, Manxi Zhou, Li Ma, Guangzhong Yin, Guangxin Chen*, Qifang Li*

Contents / Tetrahedron 70 (2014) 2295e2301 2301

COVER

Nanoporous gold skeleton catalysts (AuNPore) enables aerobic oxidation of alcohols to ketones (or aldehydes), s-bondmetathesis between R3Si-Hand H-OH to generate H2 and R3Si-OH, selective semi-hydrogenation of alkynes to cis-alkenes, selective hydrogenation of quinolines to tetrahy-droquinolines, cis-hydrosilylation of alkynes with R3SiH, and [4 + 2]cycloaddition between ortho-alkynylbenzaldehydes and alkynes leading tonaphthalene derivatives, with very high efficiencies. No leaching of gold into reaction media was observed and AuNPore can be reused severaltimes without losing its catalytic activity.

The use of nanoporous palladium skeleton catalysts (PdNPore) for Suzuki, Negishi, and Heck reactions enables far less leaching of palladium intoreactionmedia, compared to the other heterogeneous palladium catalysts. PdNPore can be reused several timeswithout losing its catalytic activity.

Nanoporous copper skeleton catalysts (CuNPore) are robust, reusable, non-leaching, and easily separable from reaction mixture in click reaction.

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