Literature DB >> 23557405

Heterocycle-heterocycle strategies: (2-nitrophenyl)isoxazole precursors to 4-aminoquinolines, 1H-indoles, and quinolin-4(1H)-ones.

Keith C Coffman1, Teresa A Palazzo, Timothy P Hartley, James C Fettinger, Dean J Tantillo, Mark J Kurth.   

Abstract

Reductive heterocycle-heterocycle (heterocycle → heterocycle; H-H) transformations that give 4-aminoquinolines, 3-acylindoles, and quinolin-4(1H)-ones from 2-nitrophenyl substituted isoxazoles are reported. When this methodology is applied to 3,5-, 4,5-, and 3,4-bis(2-nitrophenyl)isoxazoles, chemoselective heterocyclization gives quinolin-4(1H)-ones, and 4-aminoquinolines, exclusively.

Entities:  

Mesh：

Substances：

Year:  2013        PMID： 23557405      PMCID： PMC3643507          DOI： 10.1021/ol400787y

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  23 in total

Review 1.  Target-oriented and diversity-oriented organic synthesis in drug discovery.

Authors:  S L Schreiber
Journal:  Science       Date:  2000-03-17       Impact factor: 47.728

2.  Orthogonally protected thiazole and isoxazole diamino acids: an efficient synthetic route.

Authors:  Jeffrey D Butler; Keith C Coffman; Kristin T Ziebart; Michael D Toney; Mark J Kurth
Journal:  Chemistry       Date:  2010-08-09       Impact factor: 5.236

Review 3.  Diversity-oriented synthesis; a spectrum of approaches and results.

Authors:  Richard J Spandl; Andreas Bender; David R Spring
Journal:  Org Biomol Chem       Date:  2008-02-19       Impact factor: 3.876

4.  The Davis-Beirut reaction: N1,N2-disubstituted-1H-indazolones via 1,6-electrophilic addition to 3-alkoxy-2H-indazoles.

Authors:  Wayne E Conrad; Ryo Fukazawa; Makhluf J Haddadin; Mark J Kurth
Journal:  Org Lett       Date:  2011-05-25       Impact factor: 6.005

5.  A one-pot-three-step route to triazolotriazepinoindazolones from oxazolino-2H-indazoles.

Authors:  Wayne E Conrad; Kevin X Rodriguez; Huy H Nguyen; James C Fettinger; Makhluf J Haddadin; Mark J Kurth
Journal:  Org Lett       Date:  2012-07-23       Impact factor: 6.005

6.  Rh2(II)-catalyzed nitro-group migration reactions: selective synthesis of 3-nitroindoles from β-nitro styryl azides.

Authors:  Benjamin J Stokes; Sheng Liu; Tom G Driver
Journal:  J Am Chem Soc       Date:  2011-03-14       Impact factor: 15.419

Review 7.  Computational prediction of 1H and 13C chemical shifts: a useful tool for natural product, mechanistic, and synthetic organic chemistry.

Authors:  Michael W Lodewyk; Matthew R Siebert; Dean J Tantillo
Journal:  Chem Rev       Date:  2011-11-17       Impact factor: 60.622

8.  Isoxazolodihydropyridinones: 1,3-dipolar cycloaddition of nitrile oxides onto 2,4-dioxopiperidines.

Authors:  Keith C Coffman; Timothy P Hartley; Jerry L Dallas; Mark J Kurth
Journal:  ACS Comb Sci       Date:  2012-03-16       Impact factor: 3.784

9.  ZrCl4-mediated regio- and chemoselective Friedel-Crafts acylation of indole.

Authors:  Sankar K Guchhait; Maneesh Kashyap; Harshad Kamble
Journal:  J Org Chem       Date:  2011-05-13       Impact factor: 4.354

10.  Parallel Synthesis of bis-heterocyclic isoxazolylmethyl- and isoxazolinylmethylpyrazoles.

Authors:  Liping Meng; Beth A Lorsbach; Thomas C Sparks; James C Fettinger; Mark J Kurth
Journal:  J Comb Chem       Date:  2010 Jan-Feb
View more
  9 in total

1.  Davis-Beirut Reaction: Diverse Chemistries of Highly Reactive Nitroso Intermediates in Heterocycle Synthesis.

Authors:  Jie S Zhu; Makhluf J Haddadin; Mark J Kurth
Journal:  Acc Chem Res       Date:  2019-07-22       Impact factor: 22.384

2.  Diverting Reactive Intermediates Toward Unusual Chemistry: Unexpected Anthranil Products from Davis-Beirut Reaction.

Authors:  Jie S Zhu; Jung-Ho Son; Andrew P Teuthorn; Makhluf J Haddadin; Mark J Kurth; Dean J Tantillo
Journal:  J Org Chem       Date:  2017-09-28       Impact factor: 4.354

3.  Dibenzonaphthyridinones: Heterocycle-to-Heterocycle Synthetic Strategies and Photophysical Studies.

Authors:  Teresa A Palazzo; Digambara Patra; Joung S Yang; Elsy El Khoury; Mackenzie G Appleton; Makhluf J Haddadin; Dean J Tantillo; Mark J Kurth
Journal:  Org Lett       Date:  2015-11-17       Impact factor: 6.005

4.  Heterocycle-to-Heterocycle Route to Quinoline-4-amines: Reductive Heterocyclization of 3-(2-Nitrophenyl)isoxazoles.

Authors:  Keith C Coffman; Vy Duong; Alex L Bagdasarian; James C Fettinger; Makhlouf J Haddadin; Mark J Kurth
Journal:  European J Org Chem       Date:  2014-12

5.  Ruthenium-catalyzed cycloadditions of 1-haloalkynes with nitrile oxides and organic azides: synthesis of 4-haloisoxazoles and 5-halotriazoles.

Authors:  James S Oakdale; Rakesh K Sit; Valery V Fokin
Journal:  Chemistry       Date:  2014-07-24       Impact factor: 5.236

6.  Rhodium(III)-Catalyzed Redox-Neutral [3+3] Annulation of N-nitrosoanilines with Cyclopropenones: A Traceless Approach to Quinolin-4(1H)-One Scaffolds.

Authors:  Lingjun Liu; Jiyuan Li; Wenhao Dai; Feng Gao; Kaixian Chen; Yu Zhou; Hong Liu
Journal:  Molecules       Date:  2020-01-09       Impact factor: 4.411

7.  Synthesis of Cyclic Peptides in SPPS with Npb-OH Photolabile Protecting Group.

Authors:  Tingting Chen; Gang Wang; Lin Tang; Hongpeng Yang; Jing Xu; Xiaoxue Wen; Yunbo Sun; Shuchen Liu; Tao Peng; Shouguo Zhang; Lin Wang
Journal:  Molecules       Date:  2022-03-29       Impact factor: 4.411

8.  Synthesis of C4-alkynylisoxazoles via a Pd-catalyzed Sonogashira cross-coupling reaction.

Authors:  Wen Yang; Yongqi Yao; Xin Yang; Yingying Deng; Qifu Lin; Dingqiao Yang
Journal:  RSC Adv       Date:  2019-03-18       Impact factor: 4.036

9.  Crystal structures of four indole derivatives with a phenyl substituent at the 2-position and a carbonyl group at the 3-position: the C(6) N-H⋯O chain remains the same, but the weak reinforcing inter-actions are different.

Authors:  Jamie R Kerr; Laurent Trembleau; John M D Storey; James L Wardell; William T A Harrison
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2016-02-20
  9 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.