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

The Journal of organic chemistry

PubMedID: 27626809

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;.
: 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 condition 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 diverse class of ?-carbolines and benzofuro[3,2-c]pyridines using corresponding ester hydrochlorides of serine, threonine and cystine as a nitrogen source.