Synthesis of diverse indene derivatives from 1-diazonaphthalen-2(1H)-ones via thermal cascade reactions.
A sequential Wolff rearrangement of 1-diazonaphthalen-2(1H)-ones followed by trapping of the ketene intermediate with primary and aromatic amines or alcohols and phenols in the presence of various aldehydes generates 1H-indene-3-carboxamides or 1H-indene-3-carboxylates. This constitutes an unprecedented three-component coupling reaction that allows for the synthesis of functionalized indene derivatives under catalyst-free thermal conditions.
School of Chemical Engineering, Yeungnam University , Gyeongsan 712-749, Republic of Korea.
Krishna Bahadur
KB
Somai Magar
Yong Rok
YR
Lee
D000438:Alcohols / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry; D000588:Amines / Q000737:chemistry*; D001391:Azo Compounds / Q000737:chemistry*; D002384:Catalysis; D005030:Ethylenes / Q000737:chemistry; D007192:Indenes / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D013237:Stereoisomerism
D000438:Alcohols; D000447:Aldehydes; D000588:Amines; D001391:Azo Compounds; D005030:Ethylenes; D007192:Indenes; D007659:Ketones; D009281:Naphthalenes; C008223:ketene