Special Issue

Steven M. Weinreb's Special Issues, Vol. 70, No. 1, 2006

70 data found. 61 - 70 listedFirst Previous
Note | Special issue | Vol 70, No. 1, 2006, pp. 587 - 598
Published online: 17th November, 2006
DOI: 10.3987/COM-06-S(W)31
A Novel One-Pot Synthesis of N-Substituted Thieno[3,2-d]pyrimidin-4(3H)-ones

Andrew J. Peat,* Paul L. Feldman, Dulce Garrido, Yu C. Guo, and Donald L. Hertzog

*Room 3.4244, Medicinal Chemistry Department, 5 Moore Drive, Research Triangle Park, NC 27709, U.S.A.


A novel synthetic route for the construction of thieno[3,2-d]pyrimidin-4(3H)-ones has been developed with the key step involving an AlMe3-promoted ester-to-amide conversion. The yields within this initial set of analogs are comparable to those obtained via our previously reported routes and in at least one case far superior, thus serving to compliment other approaches to this useful chemical scaffold.

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Note | Special issue | Vol 70, No. 1, 2006, pp. 599 - 607
Published online: 17th October, 2006
DOI: 10.3987/COM-06-S(W)38
Synthesis of a 5-Azaindole Phosphonic Acid as a Computationally Designed Inhibitor of the Low Molecular Weight Phosphatase HCPTP

Jeremy A. Weitgenant, Isamu Katsuyama, Marinus A. Bigi, Steven J. Corden, John T. Markiewicz, Adam P. R. Zabell, Kristoff T. Homan, Olaf Wiest, Cynthia V. Stauffacher,* and Paul Helquist*

*Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, IN 46556, U.S.A.


A computationally designed inhibitor of human low molecular weight protein tyrosine phosphatase, HCPTP, was synthesized. The target compound is based on a 5-azaindole heterocyclic core bearing a phosphonic acid side chain. Its synthesis was accomplished in ten steps.

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Note | Special issue | Vol 70, No. 1, 2006, pp. 609 - 617
Published online: 17th October, 2006
DOI: 10.3987/COM-06-S(W)45
A Stereocontrolled Synthesis of (±)-β-Isosparteine

Paul R. Blakemore,* Neil R. Norcross, Stuart L. Warriner, and Peter C. Astles

*Department of Chemistry, Oregon State University, Gilbert Hall 153, Corvallis, Oregon 97331, U.S.A.


A versatile tetraoxobispidine synthon, 3,7-diallyl-2,4,6,8-tetraoxo-3,7-diazabicyclo[3.3.1]nonane (1), was converted to the title alkaloid via a synthetic sequence incorporating: imide reduction, Sakurai allylation, and ring-closing olefin metathesis reactions.

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Note | Special issue | Vol 70, No. 1, 2006, pp. 619 - 626
Published online: 2nd November, 2006
DOI: 10.3987/COM-06-S(W)53
Synthesis of 4,7-Dihydro-2H-isoindole Derivatives via Diels-Alder Reaction of Tosylacetylene

Tetsuo Okujima,* Guangnan Jin, Yusuke Hashimoto, Hiroko Yamada, Hidemitsu Uno, and Noboru Ono*

*Department of Chemistry and Biology, Graduate School or Science and Engineering, Ehime University, Matsuyama 790-8577, Japan


Diels-Alder reaction of ethynyl p-tolyl sulfone with 1,3-dienes gave the corresponding tosyl-1,4-cyclohexadienes. The resulting adducts could be converted into 4,7-dihydro-2H-isoindole derivatives including bicyclo[2.2.2]ocatadiene(BCOD)-fused pyrrole as an isoindole equivalent.

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Note | Special issue | Vol 70, No. 1, 2006, pp. 627 - 633
Published online: 17th November, 2006
DOI: 10.3987/COM-06-S(W)57
Comparative Study of X-Ray Structures and Molecular Orbital Calculations of 6-Phenyl-6-phosphapentacyclo[,4.03,7.05,10]dodecane 6-Oxide with 4-Phenyl-4-phosphatetracyclo[3.3.02,8.03,6]octane 4-Oxide

Kiyoshi Matsumoto,* Mitsuo Toda, Hirokazu Iida, and Hiroshi Hamana

*Faculty of Pharmaceutical Sciences, Chiba Institute of Science, 3 Shiomi-cho, Choshi, Chiba 288-0025, Japan


A novel P-cage type of the title compounds were discussed in terms of X-Ray analyses and molecular orbital calculations. In solid state, trans-4-phenyl-4-phosphatetracyclo[3.3.02,8.03,6]octane 4-oxide (trans-5) is much more strained and asymmetric, whereas cis-6-phenyl-6-phosphapentacyclo[,4.03,7.05,10]dodecane 6-oxides (cis-4) is less strained and highly symmetric. Molecular mechanics, semi-empirical, ab initio, and DFT calculations were used to estimate the relative energy of cis-4, trans-4, cis-5, and trans-5.

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Note | Special issue | Vol 70, No. 1, 2006, pp. 635 - 646
Published online: 17th November, 2006
DOI: 10.3987/COM-06-S(W)58
Enantioselective Synthesis of 3-Arylindan-1-ones via Intramolecular C-H Insertion Reactions of α-Diazo-β-Ketoesters Catalyzed by Chiral Dirhodium(II) Carboxylates

Yoshihiro Natori, Masahiro Anada, Seiichi Nakamura, Hisanori Nambu, and Shunichi Hashimoto*

*Laboratory of Synthetic and Industrial Chemistry, Graduate School of Life Science, Division of Life Science, Faculty of Pharmaceutical Sciences, Hokkaido University, Kita 12, Nishi 6, Kita-ku, Sapporo, Hokkaido 060-0812, Japan


A new, catalytic enantioselective route to 3-arylindan-1-ones, versatile intermediates for the synthesis of a number of bioactive and pharmaceutically interesting molecules, was developed by exploiting the chiral dirhodium(II) complex-catalyzed intramolecular C-H insertion reaction of α-diazo-β-ketoesters as a key step. Dirhodium(II) tetrakis[N-phthaloyl-(S)-tert-leucinate], Rh2(S-PTTL)4, proved to be the catalyst of choice for this process, providing enantioselectivities of up to 72% ee.

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Note | Special issue | Vol 70, No. 1, 2006, pp. 647 - 654
Published online: 17th November, 2006
DOI: 10.3987/COM-06-S(W)60
Reaction of Functionalized Azomethine Ylides with Olefinic Dipolarophiles

Keisuke Kawashima, Akikazu Kakehi, and Michihiko Noguchi*

*Department of Industrial Chemistry, Faculty of Engineering, Yamaguchi University, 2-16-1 Tokiwadai, Ube, Yamaguchi 755-8611, Japan


N-Unsubstituted pyrrolidine derivatives are prepared by the cycloaddition of an N-unsubstituted azomethine ylide in the pyrido[1,2-a]pyrimidin-4(4H)-one system and olefinic dipolarophiles. The acid treatment of the cycloadducts, pyrrolidines, caused a fission reaction to give pyrroline derivatives and the parent heterocyclic system.

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Review | Special issue | Vol 70, No. 1, 2006, pp. 655 - 679
Published online: 27th October, 2006
DOI: 10.3987/REV-06-SR(W)1
Convenient and General Microwave-Assisted Protocols for the Expedient Synthesis of Heterocycles

William D. Shipe,* Feng Yang, Zhijian Zhao, Scott E. Wolkenberg, M. Brad Nolt, and Craig W. Lindsley

*Medicinal Chemistry, Technology Enabled Synthesis Group, Merck & Co., Inc., Sumneytown Pike, West Point, PA 19486, U.S.A.


We have developed convenient and general MAOS protocols for the synthesis of functionalized 1,2,4-triazines, canthines, imidazoles, quinoxalines, pyrazines, quinoxalinones, and 5-aminooxazoles. The methodology described herein makes use of readily available building blocks, facilitating the generation of structurally diverse analog libraries to support nascent medicinal chemistry programs. Other advantages over classical heating conditions include shortened reaction times, increased yields, and the suppression of side product formation.

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Review | Special issue | Vol 70, No. 1, 2006, pp. 691 - 704
Published online: 17th November, 2006
DOI: 10.3987/REV-06-SR(W)2
Heterocyclic Inhibitors of Tumor Necrosis Factor-α Converting Enzyme (TACE)

Jeremy I. Levin

*Chemical and Screening Sciences, Wyeth Inc., 401 N. Middletown Rd., Pearl River, NY 10965, U.S.A.


A variety of heterocyclic ring systems have been prepared as scaffolds for butynyloxyphenyl sulfonamide and sulfone hydroxamic acid inhibitors of TACE enzyme. All scaffolds provided highly active TACE inhibitors, but selectivity, and cellular activity was highly scaffold dependent.

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Review | Special issue | Vol 70, No. 1, 2006, pp. 705 - 736
Published online: 1st December, 2006
DOI: 10.3987/REV-06-SR(W)3
Ring-Closing Metathesis of Heteroatom-Substituted Dienes

Richard C. D. Brown* and Vachiraporn Satcharoen

*School of Chemistry, University of Southampton, Highfield, Southampton, SO17 1BJ U.K.


The ring-closing metathesis (RCM) of dienes that contain at least one participating heteroatom-substituted olefin is reviewed (olefins substituted with O, N, S, P, Si, B, and halogen atoms will be considered). Efforts have been made to include as many relevant examples of RCM of heteroatom-substituted dienes as possible, but due to the increasing volume of research in this area, an exhaustive coverage is not intended. Attention has focussed on diene RCM reactions catalysed by ruthenium and molybdenum alkylidene complexes, although a brief discussion of some ring-closing reactions of titanium alkylidene species is provided. Other metathesis reactions such as enyne RCM, cross-metathesis and ROMP are not included.

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