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

Raj K. Siang-en Syu. Synthesis and properties of a graphene-like macrocycle based on tetraphenylethene Han Wang. Pragya Sinha.4980 Contents / Tetrahedron 70 (2014) 4979e4990 Synthesis of multi-functional alkenes via Wittig reaction with a new-type of phosphorus ylides Yi-Ling Tsai. Chia-Jui Lee. Phosphorus ylide is the key intermediate in this approach. A plausible mechanism has been proposed and the products were further converted to pyridazinone derivatives. Tingting Lin. Gautun* pp 5057e5063 . Bansal* pp 5052e5056 R1R2NH + H O O H O H O H O R1R2NH O H O H O R1R2N OH Synthesis of (S)-2-amino-7-methoxytetralin and isoindolo[1. Yu-Shiou Fan.2-a]isoquinolinone derivatives from L-aspartic acid Jon Erik Aaseng. Ji Ma. Utpal Das. Weizhi Wang* pp 5046e5051 Tandem Michael addition of amines to maleic anhydride and 1. Shu-Mei Yang. Wenwei Lin* pp 5038e5045 An efficient synthesis of multi-functional alkenes has been described starting from commercially available starting materials.3-prototropic shift: experimental and theoretical results Asha Gurjar. Odd R.

Ethan Golliard. and of routes towards b-methyl azalanthionines. Jerzy Wicha* pp 5073e5081 Studies on the synthesis of orthogonally protected azalanthionines. Application to the synthesis of moclobemide de ric Lamaty* Xavier Bantreil*. Jean Martinez. Pauline Ohlmann. Nasreddine Kanfar. synthesis. Nicolas Gehin. Keith o pp 5082e5092 TsHN R MeO2C N S CO2All PMB NHpNz Orthogonally protected Azalanthionine Iron-catalyzed benzamide formation. Fre pp 5093e5099 . photochromism and electrochemistry of a novel material with pendant photochromic units Melek Pamuk Algi. Fatih Algi* S S N S S S S N S 4981 pp 5064e5072 n S 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. Fintan Kelleher* Keith O’Brien. by ring opening of N-activated aziridine-2-carboxylates  Proinsias.Contents / Tetrahedron 70 (2014) 4979e4990 Design. Atilla Cihaner*.

Hiroyuki Minamikawa.b-unsaturated ketones: construction of chiral functionalized tetrahydroquinolines Shinae Kim. Mari Yoshizato. Mizuki Watabe. Wataru Nomura.6-disubstituted pyrene-based hexacatenar liquid crystals: columnar phase control Takuji Hirose*. Mikio Yasutake pp 5100e5108 Synthesis and photophysical properties of phenyl-sulfanylated chlororophyll derivatives Natsuki Takei. Tatsuya Tachikawa. Satoshi Ito. Masaya Denda. Misaki Morioka. Aiko Yamauchi. Takuya Tanaka. Ki-Tae Kang. Shin-ichi Sasaki. Tomohiro Tanaka. Youichi Sato. Hitoshi Tamiaki*.4982 Contents / Tetrahedron 70 (2014) 4979e4990 Effect of alkoxy terminal chain length on mesomorphism of 1. Toru Oba* pp 5109e5113 Ph Ph 3 S PhSH AIBN NH Fluorescence emission NH N N (i) HBr/AcOH (ii) PhSH HN S NH O weak emission COOMe Asymmetric domino aza-MichaeleMichael reaction of o-N-protected aminophenyl a. Akira Otaka* pp 5122e5127 . Nami Maeda. Hiroaki Takai. Koji Ebisuno. Koichi Kodama. Chiaki Komiya. Akira Shigenaga*. Sung-Gon Kim* pp 5114e5121 Development of a fluoride-responsive amide bond cleavage device that is potentially applicable to a traceable linker Jun Yamamoto. Hirokazu Tamamura.

Johnson. Souwalak Phongpaichit. Susann Pohlers. Balaich*. Russell E. Hannah A. diphenyl ether.Contents / Tetrahedron 70 (2014) 4979e4990 4983 Palladium-catalysed SuzukieMiyaura coupling reactions of Bromhexine and Ambroxol Muhammad Sharif. Jariya Sakayaroj pp 5148e5152 . Scott T. Siwaporn Satpradit. Peter Langer. Saranyoo Klaiklay. Miller. and xanthone derivatives from the soil fungus Penicillium sp. Dong Shan. Jan Lukas. Anahit Pews-Davtyan. Iacono* pp 5142e5147 Polyketide anthraquinone. Yanxing Jia* pp 5136e5141 Synthesis and thermal properties of a new styryl-functionalized pentafulvene glassy carbon precursor Endrit Shurdha. PSU-RSPG99 Vatcharin Rukachaisirikul*. 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. Arndt Rolfs*. Kawitsara Borwornwiriyapan. Gary J.

and 5-isomers Lyubov N. Mikhaleva. Trofimov* pp 5168e5174 Stereospecific synthesis of highly substituted novel carbasugar as carbonic anhydrase inhibitors: decahydronaphthalene-1.2. NO2. Mikhail I. Andrzej Jo pp 5153e5160 Synthesis of chromeno[3. Ushakov.6.2]oxazine-N-oxides via formal [4D2] cycloaddition of 3-nitro-2-trihalomethyl-2Hchromenes with cyclohexanone and pinacolone enamines Vladislav Yu. Br. Ertan S¸ahin pp 5175e5181 O O O O OH H H H HO HO OAc OH H OH OH OH . X = Cl. Korotaev. Kodess. Sosnovskikh* pp 5161e5167 O O But R N O + N O H O R O O O O CX3 R H CCl3 H O O CX3 R = H.6. Gotsko. Emilia Fornal. Maxim D.or 5-(4. Igor A. Renata Kontek Monika Nowak*. Part 1: Synthesis of 6-aminobenzo[h]quinazolinones via BuchwaldeHartwig amination from 6-bromobenzo[h]quinazolinones zwiak. Zbigniew Malinowski*.4-c][1. Neslihan Balcı.4984 Contents / Tetrahedron 70 (2014) 4979e4990 Substituted benzoquinazolinones. Sobenina. Alexey Yu. Evgeniya G.6.7-heptol Latif Kelebekli*.3. Tomilin. Alina B1aszczyk. Vyacheslav Ya.4. Boris A. Barkov.7-tetrahydroindol-2-yl)isoxazoles in two steps: a regioselective switch between 3.7-tetrahydroindoles to 3.5. Matochkina.5.5. F But NO2 R R NO2 CCl3 N O + N O NO2 CCl3 From 4. Albina I. MeO. Denis N.

Judith A.K. Atar.1-b]benzothiazoles under solvent-free conditions Amol B.8-ethanonoradamantane derivative  mez. Dmitry S. Mark A. Rivers. Jiaxi Xu* pp 5197e5206 CbzHN R R R CO2H CbzHN 7 examples SO 3H H2N SO3H 3 examples Iron fluoride: the most efficient catalyst for one-pot synthesis of 4H-pyrimido[2. Goeta. Yeon Tae Jeong* pp 5207e5213 .A. Hugh MacBride. J. T ania Go pp 5190e5196 Synthesis of enantiopure free and N-benzyloxycarbonyl-protected 3-substituted homotaurines from naturally occurring amino acids Yongpeng Zheng. Andre Ken Wade. Graham P.Contents / Tetrahedron 70 (2014) 4979e4990 4985 Studies on bis(10 -ortho-carboranyl)benzenes and bis(10 -ortho-carboranyl)biphenyls s E. Harder. Yufit. Rachel A. Howard. Ane Otermin Pelayo Camps*. Yong Seok Jeong. Fox* pp 5182e5189 Improved synthesis of a functionalized 2.

10 min O OMe P OMe R R = alkyl/aryl R = aryl/TMS N O NH R = alkyl/aryl R = aryl/H 17 examples. Durga P. Pramanik. Fanghua Ji. Santosh G. Kamat pp 5221e5233 Synthesis of a chiral phosphonium salt for the preparation of a-substituted alaninol derivatives Takashi Tsuji*. Ruchir Kant. Biaolin Yin* pp 5242e5248 R1 O R1 known method Ar NR O OH 5 O Ar NEt R2NH2 O 6 O NEt p-TsOH (20 mol %) Ar DCE. 16 h N R2 11 R1 26 examples yields up to 83% . Keisuke Suzuki.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. 105 oC. Tsuyoshi Nakamura. 10 min rt. Li Huang. Kamat. 79-90% yield Molecular iodine catalyst promoted synthesis of chromans and 4-aryl-3.4-dihydrobenzopyran-2-ones via [3D3] cyclocoupling Mayuri M. Xuehui Li. Hui Peng. Naik. Takahide Nishi pp 5234e5241 Access to fused pyrroles via the reaction of spiro-dienyl ethers with amines involving a chemoselective skeletal rearrangement Xiaoyu Zhang.D. 79-81% yield O OMe P OMe N R KOH (1 eq) MeOH MeOH rt. Tilve*. Namrata Rastogi* pp 5214e5220 O R O O HN MeO MeO P R OMe N R O R R Me KOH (1 eq) R O R = aryl 2 examples. Vijayendra P.

Berthold Kersting* pp 5254e5259 Sulfation of deoxynivalenol. Erwin Rosenberg. Johannes Fro pp 5260e5266 A mild and efficient AgSbF6-catalyzed synthesis of fully substituted pyrroles through a sequential propargylation/amination/cycloisomerization reaction Satheesh Gujarathi. Christian Hametner. €hlich Gerhard Adam. Xin-Yan Lin. and T2-toxin Philipp Fruhmann*. Hannes Mikula. Hua-Jian Xu* pp 5249e5253 Synthesis of calix[4]arene-based polycarboxylate ligands and their chemical immobilization onto controlled-pore glass Sebastian Haupt. Michael Sulyok. Maria Poetsch. Howard Hendrickson.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. Xingui Liu. Marcel Handke. Lin Song. its acetylated derivatives. Guangrong Zheng* pp 5267e5273 . Rudolf Krska. Julia Weber. Benedikt Warth. Philipp Skrinjar. Robert Kuhnert. Jian Hao.

3-dihydroquinazolin-4(1H)-ones and quinazolin-4(3H)ones under ultrasound irradiation in aqueous ethanol under ultrasound irradiation in aqueous ethanol Jin Zhang*. Alberto Baggioli. Lindsay R. Steig A. Yangmin Ma*. Raffaella Soave. Comstock* pp 5291e5297 Free-radical selective functionalization of 1. Bremner-Hay. Natalie K. Stefano V. Zuckerman. Ivan Wlassics. Francesco Venturini. Cristian Gambarotti. Michael Egger.and alkyne-bearing N-mustard analogs of S-adenosyl-L-methionine Mohamed Ramadan.4-naphthoquinones by perfluorodiacyl peroxides Maurizio Sansotera*. Hewitt. Joseph P. Konopelski* pp 5283e5290 Synthesis and evaluation of N6-substituted azide. Antonino Famulari. Carlson. Walter Navarrini pp 5298e5309 .4988 Contents / Tetrahedron 70 (2014) 4979e4990 CuO nanoparticles catalyzed simple and efficient synthesis of 2. Weitao Wang. Meille. Decheng Ren. Nathaniel B. Hao Wu pp 5274e5282 Preparation of fused b-lactams through Weinreb amide a-anions William M.

Monika Knittl. Artur M. Silva* pp 5310e5320 Formation of 3-acyloxy-g-butyrolactones from 4-pentenols in vanadium-catalyzed oxidations €nges.M. Petra Bo pp 5332e5338 *Corresponding author Supplementary data available via ScienceDirect .S. Silva*. Rossmann.3-diarylacridin-9(10H)-one and (E)-2-aryl-4-styrylfuro[3.Contents / Tetrahedron 70 (2014) 4979e4990 4989 New synthetic methods for 2.2-c]quinoline derivatives Vera L. Georg Stapf. Eva C. Maike Do pp 5321e5331 Highly syn selective addition of aqueous HBr to hydrophobically shielded arylalkynes €hrer Rudolf Knorr*. Jens Hartung* Matthias Amberg.

Research Alert. Beilstein. Full text available on ScienceDirectÒ ISSN 0040-4020 . Current Contents: Life Sciences.sciencedirect.sciencedirect. Abstracted/indexed in: AGRICOLA. BIOSIS Previews. Current Contents: Physical. Derwent Drug File. Chemical and Earth Sciences. Ei compendex. PASCAL. EMBASE/ Excerpta Medline. Also covered in the abstract and citation database SCOPUSÒ. Science Citation Index. on-line from ScienceDirect.com ScienceDirect Full text of this journal is available.com for more information. Visit www. CAB Abstracts. SciSearch.4990 Contents / Tetrahedron 70 (2014) 4979e4990 Available online at www. Current Contents Search. Chemical Abstracts.