Regio- and Stereoselective Domino Synthesis of Oxazolo Fused Pyridoindoles and Benzofurooxazolo Pyridines from ortho-Alkynylarylaldehydes.
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.
Synthetic Organic Chemistry Research Laboratory, Department of Chemistry, University of Delhi , Delhi 110007, India.
Shilpi
S
Pal
Synthetic Organic Chemistry Research Laboratory, Department of Chemistry, University of Delhi , Delhi 110007, India.
Deepak
D
Choudhary
Synthetic Organic Chemistry Research Laboratory, Department of Chemistry, University of Delhi , Delhi 110007, India.
Mohit
M
Jainth
Synthetic Organic Chemistry Research Laboratory, Department of Chemistry, University of Delhi , Delhi 110007, India.
Sonu
S
Kumar
Chapman University School of Pharmacy , Harry and Diane Rinker Health Science Campus, 9401 Jeronimo Road, Irvine, California 92618, United States.
Rakesh K
RK
Tiwari
Synthetic Organic Chemistry Research Laboratory, Department of Chemistry, University of Delhi , Delhi 110007, India.
Akhilesh K
AK
Verma