Literature DB >> 20664860

An unusual reactivity of BBr(3): Accessing tetrahydroisoquinoline units from N-phenethylimides.

Jayaraman Selvakumar1, Alexandros Makriyannis, Chinnasamy Ramaraj Ramanathan.   

Abstract

Isoindoloisoquinalinone, pyrroloisoquinolinone and benzo[a]quinolizinone units are constructed via intramolecular cyclization of the methoxy substituted N-phenethylimides using BBr(3).

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Year:  2010        PMID： 20664860      PMCID： PMC5772845          DOI： 10.1039/c0ob00269k

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  14 in total

Review 1.  Chemistry and biology of the tetrahydroisoquinoline antitumor antibiotics.

Authors:  Jack D Scott; Robert M Williams
Journal:  Chem Rev       Date:  2002-05       Impact factor: 60.622

2.  Cyclizations of N-acyliminium ions.

Authors:  Bruce E Maryanoff; Han-Cheng Zhang; Judith H Cohen; Ignatius J Turchi; Cynthia A Maryanoff
Journal:  Chem Rev       Date:  2004-03       Impact factor: 60.622

3.  Conjugate additions of sulfur-stabilized anions to unsaturated lactams. Synthesis of polyfunctionalized benzo[a]quinolizinone systems.

Authors:  Eva García; Esther Lete; Nuria Sotomayor
Journal:  J Org Chem       Date:  2006-09-01       Impact factor: 4.354

4.  Metalation vs Nucleophilic Addition in the Reactions of N-Phenethylimides with Organolithium Reagents. Ready Access to Isoquinoline Derivatives via N-Acyliminium Ions and Parham-Type Cyclizations.

Authors:  M. Isabel Collado; Izaskun Manteca; Nuria Sotomayor; María-Jesús Villa; Esther Lete
Journal:  J Org Chem       Date:  1997-04-04       Impact factor: 4.354

5.  New approaches for the synthesis of erythrinan alkaloids.

Authors:  Fengzhi Zhang; Nigel S Simpkins; Alexander J Blake
Journal:  Org Biomol Chem       Date:  2009-03-24       Impact factor: 3.876

6.  Synthesis of benzo-fused lactams and lactones via Ru(II)-catalyzed cycloaddition of amide- and ester-tethered alpha,omega-diynes with terminal alkynes: electronic directing effect of internal conjugated carbonyl group.

Authors:  Yoshihiko Yamamoto; Keisuke Kinpara; Tomoaki Saigoku; Hisao Nishiyama; Kenji Itoh
Journal:  Org Biomol Chem       Date:  2004-04-07       Impact factor: 3.876

7.  Enantioselective synthesis of schulzeines B and C via a beta-lactone-derived surrogate for bishomoserine aldehyde.

Authors:  Gang Liu; Daniel Romo
Journal:  Org Lett       Date:  2009-03-05       Impact factor: 6.005

8.  Schulzeines A-C, new alpha-glucosidase inhibitors from the marine sponge Penares schulzei.

Authors:  Kentaro Takada; Taisuke Uehara; Yoichi Nakao; Shigeki Matsunaga; Rob W M van Soest; Nobuhiro Fusetani
Journal:  J Am Chem Soc       Date:  2004-01-14       Impact factor: 15.419

9.  Total synthesis of the alpha-glucosidase inhibitors schulzeine A, B, and C and a structural revision of schulzeine A.

Authors:  Edward G Bowen; Duncan J Wardrop
Journal:  J Am Chem Soc       Date:  2009-05-06       Impact factor: 15.419

10.  Total syntheses of schulzeines B and C.

Authors:  Mukund K Gurjar; Chinmoy Pramanik; Debabrata Bhattasali; C V Ramana; Debendra K Mohapatra
Journal:  J Org Chem       Date:  2007-07-14       Impact factor: 4.354
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  3 in total

1.  Total synthesis and biological evaluation of an antifungal tricyclic o-hydroxy-p-quinone methide diterpenoid.

Authors:  Jinhua Huang; Dylan Foyle; Xiaorong Lin; Jiong Yang
Journal:  J Org Chem       Date:  2013-09-05       Impact factor: 4.354

2.  Brønsted acid-mediated cyclization-dehydrosulfonylation/reduction sequences: An easy access to pyrazinoisoquinolines and pyridopyrazines.

Authors:  Ramana Sreenivasa Rao; Chinnasamy Ramaraj Ramanathan
Journal:  Beilstein J Org Chem       Date:  2017-03-07       Impact factor: 2.883

3.  Crystal structure, DFT calculations and evaluation of 2-(2-(3,4-dimethoxyphenyl)ethyl)isoindoline-1,3-dione as AChE inhibitor.

Authors:  Erik Andrade-Jorge; José Bribiesca-Carlos; Francisco J Martínez-Martínez; Marvin A Soriano-Ursúa; Itzia I Padilla-Martínez; José G Trujillo-Ferrara
Journal:  Chem Cent J       Date:  2018-06-25       Impact factor: 4.215
  3 in total

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