Literature DB >> 16323862

Microwave-assisted concise total syntheses of quinazolinobenzodiazepine alkaloids.

Ji-Feng Liu1, Mira Kaselj, Yuko Isome, Jennifer Chapnick, Bailin Zhang, Grace Bi, Daniel Yohannes, Libing Yu, Carmen M Baldino.   

Abstract

[reactions: see text] One-pot total syntheses of the quinazolinobenzodiazepine alkaloids sclerotigenin (1), (+/-)-circumdatin F (2), and (+/-)-asperlicin C (3) via novel microwave-assisted domino reactions were achieved in 55%, 32%, and 20% yields, respectively, from commercially available starting materials. A two-step total synthesis of (+/-)-benzomalvin A (4) was accomplished with an overall yield of 16%. Additionally, analogues of circumdatin E were synthesized via the three-component one-pot sequential reactions promoted by microwave irradiation. Finally, a two-step formal total synthesis of (+/-)-asperlicin E (5) was also realized by using this microwave-assisted protocol.

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Year:  2005        PMID: 16323862     DOI: 10.1021/jo051876x

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  8 in total

Review 1.  Controlled microwave heating in modern organic synthesis: highlights from the 2004-2008 literature.

Authors:  C Oliver Kappe; Doris Dallinger
Journal:  Mol Divers       Date:  2009-04-21       Impact factor: 2.943

Review 2.  Biosynthesis, synthesis, and biological activities of pyrrolobenzodiazepines.

Authors:  Barbara Gerratana
Journal:  Med Res Rev       Date:  2010-06-13       Impact factor: 12.944

3.  Antioxidant, anticancer and electrochemical redox properties of new bis(2,3-dihydroquinazolin-4(1H)-one) derivatives.

Authors:  Paramasivam Sivaguru; Kandasamy Parameswaran; Appaswami Lalitha
Journal:  Mol Divers       Date:  2017-05-05       Impact factor: 2.943

4.  Assembly of asperlicin peptidyl alkaloids from anthranilate and tryptophan: a two-enzyme pathway generates heptacyclic scaffold complexity in asperlicin E.

Authors:  Stuart W Haynes; Xue Gao; Yi Tang; Christopher T Walsh
Journal:  J Am Chem Soc       Date:  2012-10-09       Impact factor: 15.419

5.  Fluorous synthesis of sclerotigenin-type benzodiazepine-quinazolinones.

Authors:  Wei Zhang; John P Williams; Yimin Lu; Tadamichi Nagashima; Qainli Chu
Journal:  Tetrahedron Lett       Date:  2007-01-22       Impact factor: 2.415

Review 6.  Microwave multicomponent synthesis.

Authors:  Helmut M Hügel
Journal:  Molecules       Date:  2009-12-01       Impact factor: 4.411

Review 7.  Microwave-Assisted Synthesis of Quinazolines and Quinazolinones: An Overview.

Authors:  Leyla Mohammadkhani; Majid M Heravi
Journal:  Front Chem       Date:  2020-11-16       Impact factor: 5.221

8.  One-pot synthesis of novel 1H-pyrimido[4,5-c][1,2]diazepines and pyrazolo[3,4-d]pyrimidines.

Authors:  Dipak Prajapati; Partha P Baruah; Baikuntha J Gogoi; Jagir S Sandhu
Journal:  Beilstein J Org Chem       Date:  2006-03-23       Impact factor: 2.883

  8 in total

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