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1. Convergent synthesis of Carpatamide-A: Cytotoxic arylamine derivative from marine derived Streptomyces sp.

Author:
Burman, Rohani Prasad; Gupta, Shantanu; Bhatti, Jyoti; Verma, Krishan; Rajak, Devendra; Gill, Manjinder Singh
Source:
Natural product research 2019 v.33 no.8 pp. 1147-1157
ISSN:
1478-6427
Subject:
benzaldehyde,   etc   ; Streptomyces; cytotoxicity; demethylation; methylation;     Show all 5 Subjects
Abstract:
... First total synthesis of carpatamide-A 7a, cytotoxic arylamine derivative isolated from marine derived Streptomyces sp., was achieved in twelve steps with overall yield of 24% with seven longest linear steps. In the penultimate step, dienoic acid 13 and an amino-phenylpropionic acid methyl ester core 21 were coupled to synthesize methylated derivativative of carpatamide-A 22 followed by demethylat ...
DOI:
10.1080/14786419.2018.1460837

2. Efficient One-Pot Synthesis of End-Functionalized trans-Stereoregular Polydiene Macromonomers

Author:
Georges, Sébastien; Hashmi, Obaid Hasan; Bria, Marc; Zinck, Philippe; Champouret, Yohan; Visseaux, Marc
Source:
Macromolecules 2019 v.52 no.3 pp. 1210-1219
ISSN:
1520-5835
Subject:
benzaldehyde,   etc   ; benzophenones; isoprene; myrcene; polymers; styrene; synthesis;     Show all 7 Subjects
Abstract:
... End-functionalized 1,4-trans-polydienes (isoprene and myrcene) were prepared by means of a neodymium-mediated continuous polymerization–functionalization process. A chain transfer stage was essential to get a high level of functionalization of the polymer. The living 1,4-trans-stereoregular polymer chain was reacted with benzophenone to afford up to 97% −CPh₂OH end-group with isoprene, while in th ...
DOI:
10.1021/acs.macromol.8b01520

3. Facile and practical synthesis of π-extended oxepins by benzannulation and intramolecular cyclization

Author:
Umeda, Rui; Shimizu, Yuji; Ida, Yuta; Ikeshita, Masahiro; Suzuki, Shuichi; Naota, Takeshi; Nishiyama, Yutaka
Source:
Tetrahedron letters 2019 v.60 no.2 pp. 183-186
ISSN:
0040-4039
Subject:
benzaldehyde,   etc   ; chemical structure; cyclization reactions; optical properties;     Show all 4 Subjects
Abstract:
... π-Extended oxepins 1 and dimer 8 were synthesized by the benzannulation of the corresponding asymmetric diarylacetylene derivatives and 2-(phenylethynyl)benzaldehyde followed by the Cu-catalyzed intramolecular cyclization. The optical properties of the π-extended oxepins 1 and 8 are also investigated. ...
DOI:
10.1016/j.tetlet.2018.12.008

4. PTSA catalyzed synthesis of functionalized dipyrazolo[1,5]diazocine-3,8-diones via the reaction of 3-aminopyrazolone with benzaldehyde derivatives

Author:
Khodabakhshi, Mohammad Reza; Moghaddam, Firouz Matloubi; Kiamehr, Mostafa
Source:
Tetrahedron letters 2018 v.59 no.51 pp. 4503-4508
ISSN:
0040-4039
Subject:
benzaldehyde,   etc   ; chemical reactions; chemical structure;     Show all 3 Subjects
Abstract:
... A simple procedure for the synthesis of dipyrazolo[1,5]diazocine-3,8-diones was developed via the one-pot reaction of 3-aminopyrazolone with substituted benzaldehydes in the presence of catalytic p-toluenesulfonic acid (PTSA). ...
DOI:
10.1016/j.tetlet.2018.11.022

5. Silver-Catalyzed Radical Cascade Cyclization toward 1,5-/1,3-Dicarbonyl Heterocycles: An Atom-/Step-Economical Strategy Leading to Chromenopyridines and Isoxazole-/Pyrazole-Containing Chroman-4-Ones

Author:
Hu, Hao; Chen, Xiaolan; Sun, Kai; Wang, Junchao; Liu, Yan; Liu, Hui; Fan, Lulu; Yu, Bing; Sun, Yuanqiang; Qu, Lingbo; Zhao, Yufen
Source:
Organic letters 2018 v.20 no.19 pp. 6157-6160
ISSN:
1523-7052
Subject:
benzaldehyde,   etc   ; cyclization reactions; indans; moieties;     Show all 4 Subjects
Abstract:
... A novel and convenient silver-catalyzed radical cascade cyclization toward a large variety of 1,5-/1,3-dicarbonyl heterocycles containing a chroman-4-one, indanone, or 2,3-dihydroquinolin-4(1H)-one moiety was developed, by reacting various 2-functionalized benzaldehydes, including 2-allyloxy benzaldehydes, 2-allyl benzaldehyde, and 2-N(Ts)CH₂–CH═CH₂ substituted benzaldehyde, with 1,3-dicarbonyl co ...
DOI:
10.1021/acs.orglett.8b02627

6. Rh(III)-Catalyzed Enaminone-Directed C–H Coupling with α-Diazo-α-phosphonoacetate for Reactivity Discovery: Fluoride-Mediated Dephosphonation for C–C Coupling Reactions

Author:
Song, Chao; Yang, Chen; Zeng, Hua; Zhang, Wenjing; Guo, Shan; Zhu, Jin
Source:
Organic letters 2018 v.20 no.13 pp. 3819-3823
ISSN:
1523-7052
Subject:
benzaldehyde,   etc   ; chemical reactions; chemical structure;     Show all 3 Subjects
Abstract:
... Rh(III)-catalyzed enaminone-directed C–H coupling with α-diazo-α-phosphonoacetate has been used for the identification of fluoride-mediated dephosphonation C–C coupling reactivity for the synthesis of 4-hydroxy-1-naphthoates. Intermolecular C–C coupling of α-phosphonoacetate and benzaldehyde for (E)-selective α,β-unsaturated ester synthesis has also been achieved. ...
DOI:
10.1021/acs.orglett.8b01406

7. Changes in volatile composition during the processing and storage of black ripe olives

Author:
López-López, Antonio; Cortés-Delgado, Amparo; de Castro, Antonio; Sánchez, Antonio Higinio; Montaño, Alfredo
Source:
Food research international 2019 v.125 pp. 108568
ISSN:
0963-9969
Subject:
benzaldehyde,   etc   ; cultivars; dimethyl sulfide; ethanol; ethyl acetate; olives; volatile compounds;     Show all 7 Subjects
Abstract:
... The present study revealed the effects of each step of black ripe olive processing (preservation, darkening, packing + sterilization) and storage on the volatile composition of two olive cultivars (Manzanilla and Hojiblanca). The preservation step enriched the volatile profile of the olives, mainly in ethyl acetate, methyl acetate, and ethanol. The darkening step produced the total or partial elim ...
DOI:
10.1016/j.foodres.2019.108568

8. Synthesis of chiral crown ethers derived from d-galactose and their application in enantioselective reactions

Author:
Rapi, Zsolt; Nemcsok, Tamás; Bagi, Péter; Keglevich, György; Bakó, Péter
Source:
Tetrahedron 2019 v.75 no.30 pp. 3993-4004
ISSN:
0040-4020
Subject:
benzaldehyde,   etc   ; catalysts; chemical structure; enantioselectivity; epoxidation reactions; ethers; galactose;     Show all 7 Subjects
Abstract:
... A few new α- and β-d-galactopyranoside-based chiral lariat ethers of monoaza-15-crown-5 type were synthesized. These macrocycles proved to be efficient catalysts in a few asymmetric reactions under mild phase transfer conditions. The catalytic effect of the lariat ethers with methoxy, ethoxy, isopropoxy and aryloxy substituents on the C-1 of the sugar unit in both α and β positions was compared. I ...
DOI:
10.1016/j.tet.2019.06.020

9. Chiral zinc amidate catalyzed additions of diethylzinc to aldehydes

Author:
Zhang, Jinxia; Li, Shasha; Zheng, Xinxin; Li, Hongjie; Jiao, Peng
Source:
Tetrahedron letters 2019 v.60 no.29 pp. 1913-1917
ISSN:
0040-4039
Subject:
benzaldehyde,   etc   ; catalysts; catalytic activity; chemical reactions; crystal structure; ligands; zinc;     Show all 7 Subjects
Abstract:
... A series of bifunctional spiro ligands bearing “carboxamide–phosphine oxide” groups and ethylzinc carboxamidates from these ligands as catalysts for Et2Zn additions to aldehydes were reported. Excellent yields were obtained with moderate ee′s in Et2Zn additions to benzaldehyde derivatives, implying effectiveness of our newly designed catalytic structures as well as mediocre stereocontrol by these ...
DOI:
10.1016/j.tetlet.2019.06.031

10. Transient directing ligand- and solvent-controlled C–H/C–H cross-coupling/quaternization cyclization/dequaternization of benzaldehydes with thiophenes

Author:
Sun, Denan; Du, Jiping; Fang, Hao; Lan, Jingbo; Wu, Di; You, Jingsong
Source:
Chemical communications 2019 v.55 no.52 pp. 7518-7521
ISSN:
1364-548X
Subject:
benzaldehyde,   etc   ; chemoselectivity; cross-coupling reactions; ligands; rhodium; solvents; thiophenes;     Show all 7 Subjects
Abstract:
... Rh(iii)-Catalyzed oxidative C–H/C–H cross-coupling between benzaldehydes and thiophenes has been accomplished for the first time. In such reactions, transient directing ligands (TDLs) can not only promote ortho-C–H activation, but can also control the chemoselectivity through a suitable combination of different solvents. ...
DOI:
10.1039/c9cc04017j

11. Silylene induced cooperative B–H bond activation and unprecedented aldehyde C–H bond splitting with amidinate ring expansion

Author:
Swamy, V. S. V. S. N.; Raj, K. Vipin; Vanka, Kumar; Sen, Sakya S.; Roesky, Herbert W.
Source:
Chemical communications 2019 v.55 no.24 pp. 3536-3539
ISSN:
1364-548X
Subject:
benzaldehyde,   etc   ; carbon-hydrogen bond activation; chemical bonding; chemical reactions; silicon;     Show all 5 Subjects
Abstract:
... The addition of HBpin to PhC(NtBu)₂SiN(SiMe₃)₂ (1) results in the cleavage of the B–H bond in a cooperative fashion across the Si and amidinate-C sites. The reaction of 1 with benzaldehyde led to C–H bond activation with amidinate ring expansion leading to a five-membered heterocycle. In case of 4-fluorobenzaldehyde, a C–C bond coupling takes place leading to a dioxasilolane derivative as the majo ...
DOI:
10.1039/c9cc00296k

12. An environmentally benign multi-component reaction: regioselective synthesis of fluorinated 2-aminopyridines using diverse properties of the nitro group

Author:
Du, Xuan-Xuan; Zi, Quan-Xing; Wu, Yu-Meng; Jin, Yi; Lin, Jun; Yan, Sheng-Jiao
Source:
Green chemistry 2019 v.21 no.6 pp. 1505-1516
ISSN:
1463-9270
Subject:
benzaldehyde,   etc   ; cyclization reactions; green chemistry; medicinal properties; nitro compounds; regioselectivity;     Show all 6 Subjects
Abstract:
... An efficient and concise one-pot procedure was developed for the synthesis of two kinds of fluorinated 2-aminopyridine compounds, 4 and 5, based on the reactions of different types of 1,1-enediamines (EDAMs), 1, with a variety of benzaldehyde derivatives, 2, and 1,3-dicarbonyl compounds, 3, involving the Knoevenagel, Michael and cyclization reactions under heating. This protocol is especially suit ...
DOI:
10.1039/c8gc03698e

13. Ultrasensitive detection of volatile aldehydes with chemi-ionization-coupled time-of-flight mass spectrometry

Author:
Yang, Bo; Xu, Ce; Shu, Jinian; Li, Zhen; Zhang, Haixu; Ma, Pengkun
Source:
Talanta 2019 v.194 pp. 888-894
ISSN:
0039-9140
Subject:
benzaldehyde,   etc   ; detection limit; humidity; ionization; ions; mass spectrometry; methylene chloride;     Show all 7 Subjects
Abstract:
... The chemi-ionization reaction is a high-efficiency pathway to produce molecular ions in plasma, however, it has rarely been applied in mass spectrometry to directly produce analyte ions. In this study, a novel chemi-ionization technique for mass spectrometry was applied for the direct and ultrasensitive detection of gaseous aldehydes. The ionization technique was enacted by a recently observed che ...
DOI:
10.1016/j.talanta.2018.11.004

14. Multicomponent domino protocol for the stereoselective synthesis of novel pyrrolo[3,2-c]quinolinone hybrid heterocycles

Author:
Arumugam, Natarajan; Almansour, Abdulrahman I.; Kumar, Raju Suresh; Altaf, Mohammad; Mahalingam, S.M.; Periyasami, Govindasami; Menéndez, J. Carlos; Ali Al-Aizari, Abdul Jaleel Mohammad
Source:
Tetrahedron letters 2019 v.60 no.8 pp. 602-605
ISSN:
0040-4039
Subject:
benzaldehyde,   etc   ; chemical structure; cycloaddition reactions; phenylalanine; quinolones; stereoselective synthesis;     Show all 6 Subjects
Abstract:
... A series of structurally intriguing novel pyrrolo[3,2-c]quinolinone heterocyclic hybrids have been synthesized for the first time via a one-pot multicomponent domino reaction sequence that involves a 1,3-dipolar cycloaddition and two subsequent annulation steps. Baylis-Hillman adducts derived from various substituted benzaldehyde and methyl acrylate in presence of DABCO were used as a dipolarophil ...
DOI:
10.1016/j.tetlet.2019.01.035

15. Multicomponent Synthesis of Isoindolinones by Rhᴵᴵᴵ Relay Catalysis: Synthesis of Pagoclone and Pazinaclone from Benzaldehyde

Author:
Zhang, Yan; Zhu, Haiqian; Huang, Yuting; Hu, Qi; He, Yu; Wen, Yihang; Zhu, Gangguo
Source:
Organic letters 2019 v.21 no.5 pp. 1273-1277
ISSN:
1523-7052
Subject:
benzaldehyde,   etc   ; catalytic activity; chemical reactions; chemical structure; tranquilizers;     Show all 5 Subjects
Abstract:
... A practical one-pot isoindolinone synthesis enabled by Rhᴵᴵᴵ catalysis was developed. The advantage of this protocol is that it does not require pre-preparation of amide substrates, because Rhᴵᴵᴵ participates in two reactions independently. This mild, operationally multicomponent process transforms a wide variety of commercially available aldehydes into the corresponding γ-lactams in good yields, ...
DOI:
10.1021/acs.orglett.8b04026

16. B(C₆F₅)₃-Catalyzed Group Transfer Polymerization of Acrylates Using Hydrosilane: Polymerization Mechanism, Applicable Monomers, and Synthesis of Well-Defined Acrylate Polymers

Author:
Chen, Yougen; Jia, Qun; Ding, Yuansheng; Sato, Shin-ichiro; Xu, Liang; Zang, Chunyu; Shen, Xiande; Kakuchi, Toyoji
Source:
Macromolecules 2019 v.52 no.3 pp. 844-856
ISSN:
1520-5835
Subject:
benzaldehyde,   etc   ; Lewis acids; Lewis bases; acrylates; catalysts; composite polymers; copolymerization;     Show all 7 Subjects
Abstract:
... We demonstrated the B(C₆F₅)₃-catalyzed group transfer polymerization (GTP) of acrylate monomers with hydrosilane by the in situ formation of silyl ketene acetals (SKAs) as the initiator by the B(C₆F₅)₃-catalyzed 1,4-hydrosilylation of acrylate monomers and hydrosilane. In addition, this new GTP method was clarified in terms of the polymerization mechanism, scope and limitation of the acrylate mono ...
DOI:
10.1021/acs.macromol.8b02245

17. An iodine/DMSO-catalyzed sequential one-pot approach to 2,4,5-trisubstituted-1H-imidazoles from α-methylene ketones

Author:
Jayram, Janeeka; Jeena, Vineet
Source:
RSC advances 2018 v.8 no.66 pp. 37557-37563
ISSN:
2046-2069
Subject:
benzaldehyde,   etc   ; dimethyl sulfoxide; imidazoles; iodine; ketones;     Show all 5 Subjects
Abstract:
... A sequential one-pot approach to 2,4,5-trisubstituted imidazoles has been developed from α-methylene ketones and aldehydes. This methodology employs air-moisture stable reaction conditions and an inexpensive iodine/DMSO system affording a diverse range of known and novel (substrate scope) 2,4,5-trisubstituted imidazoles in moderate to excellent yields. The iodine/DMSO system was extended to the do ...
DOI:
10.1039/c8ra07238h

18. Binary Alkoxide Ionic Liquids

Author:
McNeice, Peter; Marr, Andrew C.; Marr, Patricia C.; Earle, Martyn J.; Seddon, Kenneth R.
Source:
ACS sustainable chemistry & engineering 2018 v.6 no.11 pp. 13676-13680
ISSN:
2168-0485
Subject:
benzaldehyde,   etc   ; acetone; condensation reactions; ionic liquids; pyridines;     Show all 5 Subjects
Abstract:
... Strongly basic, stable ionic liquids are rare. We report the synthesis of a series of stable binary alkoxide ionic liquids. The Hammett basicity of these ionic liquids is comparable to or greater than traditional bases such as pyridine and NaOMe. The ionic liquids catalyze the Knoevenagel condensation of malononitrile and benzaldehyde, with the best system displaying higher activity than pyridine ...
DOI:
10.1021/acssuschemeng.8b04299

19. Reductive coupling of two aldehydes to unsymmetrical E-alkenes via phosphaalkene and phosphinate intermediates

Author:
Mai, Juri; Arkhypchuk, Anna I.; Gupta, Arvind Kumar; Ott, Sascha
Source:
Chemical communications 2018 v.54 no.52 pp. 7163-7166
ISSN:
1364-548X
Subject:
benzaldehyde,   etc   ; cross-coupling reactions; electronics; oxidation; stilbenes;     Show all 5 Subjects
Abstract:
... Stilbenes with push–pull electronics are directly accessible from an electron-rich and an electron-deficient benzaldehyde in a novel reductive aldehyde cross-coupling reaction. The one-pot procedure is enabled by the oxidation of a transient phosphinite to the corresponding phosphinate which exhibits sufficient reactivity towards deactivated aldehydes. ...
DOI:
10.1039/c8cc04218g

20. Diverse ortho-C(sp2)–H Functionalization of Benzaldehydes Using Transient Directing Groups

Author:
Liu, Xi-Hai; Park, Hojoon; Hu, Jun-Hao; Hu, Yan; Zhang, Qun-Liang; Wang, Bao-Long; Sun, Bing; Yeung, Kap-Sun; Zhang, Fang-Lin; Yu, Jin-Quan
Source:
Journal of the American Chemical Society 2017 v.139 no.2 pp. 888-896
ISSN:
1520-5126
Subject:
benzaldehyde,   etc   ; bromination; catalysts; chlorination; drugs;     Show all 5 Subjects
Abstract:
... Pd-catalyzed C–H functionalizations promoted by transient directing groups remain largely limited to C–H arylation only. Herein, we report a diverse set of ortho-C(sp²)–H functionalizations of benzaldehyde substrates using the transient directing group strategy. Without installing any auxiliary directing group, Pd(II)-catalyzed C–H arylation, chlorination, bromination, and Ir(III)-catalyzed amidat ...
DOI:
10.1021/jacs.6b11188