Display options
Cite
Pal S, Choudhary D, Jainth M, et al. Regio- and Stereoselective Domino Synthesis of Oxazolo Fused Pyridoindoles and Benzofurooxazolo Pyridines from ortho-Alkynylarylaldehydes. J Org Chem. 2016;81(19):9356-9371doi: 10.1021/acs.joc.6b02062.
Pal, S., Choudhary, D., Jainth, M., Kumar, S., Tiwari, R. K., & Verma, A. K. (2016). Regio- and Stereoselective Domino Synthesis of Oxazolo Fused Pyridoindoles and Benzofurooxazolo Pyridines from ortho-Alkynylarylaldehydes. The Journal of organic chemistry, 81(19), 9356-9371. https://doi.org/10.1021/acs.joc.6b02062
Pal, Shilpi, et al. "Regio- and Stereoselective Domino Synthesis of Oxazolo Fused Pyridoindoles and Benzofurooxazolo Pyridines from ortho-Alkynylarylaldehydes." The Journal of organic chemistry vol. 81,19 (2016): 9356-9371. doi: https://doi.org/10.1021/acs.joc.6b02062
Pal S, Choudhary D, Jainth M, Kumar S, Tiwari RK, Verma AK. Regio- and Stereoselective Domino Synthesis of Oxazolo Fused Pyridoindoles and Benzofurooxazolo Pyridines from ortho-Alkynylarylaldehydes. J Org Chem. 2016 Oct 07;81(19):9356-9371. doi: 10.1021/acs.joc.6b02062. Epub 2016 Sep 26. PMID: 27626809.
Copy Download .nbib Format: NLM
Share it on

J Org Chem. 2016 Oct 07;81(19):9356-9371. doi: 10.1021/acs.joc.6b02062. Epub 2016 Sep 26.

Regio- and Stereoselective Domino Synthesis of Oxazolo Fused Pyridoindoles and Benzofurooxazolo Pyridines from ortho-Alkynylarylaldehydes.

The Journal of organic chemistry

Shilpi Pal, Deepak Choudhary, Mohit Jainth, Sonu Kumar, Rakesh K Tiwari, Akhilesh K Verma

Affiliations

  1. Synthetic Organic Chemistry Research Laboratory, Department of Chemistry, University of Delhi , Delhi 110007, India.
  2. Chapman University School of Pharmacy , Harry and Diane Rinker Health Science Campus, 9401 Jeronimo Road, Irvine, California 92618, United States.

PMID: 27626809 DOI: 10.1021/acs.joc.6b02062

Abstract

An environmentally benign Au(III)-catalyzed regio- and stereoselective domino synthesis of oxazolo fused pyridoindoles 7a-v and benzofurooxazolo pyridines 8a-n by the reaction of o-alkynylaldehydes 4a-t and 5a-k with (S)-phenylglycinol 6a and (R)-phenylglycinol 6b under mild reaction conditions using water as reaction medium is reported. The reaction proceeded via selective C-N bond formation on the more electrophilic alkynyl carbon through 6-endo-dig cyclization. The reaction tolerates a wide variety of functional groups. The developed chemistry has been successfully extended for the synthesis of a diverse class of γ-carbolines and benzofuro[3,2-c]pyridines using corresponding ester hydrochlorides of serine, threonine, and cystine as a nitrogen source.

Publication Types