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First reactions of vinylindoles with diethyl mesoxalate, nitrosobenzene, and chlorosulfonyl isocyanate: New functionalized and [b]annellated indoles

✍ Scribed by Ulf Pindur; Myung-Hwa Kim


Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
803 KB
Volume
45
Category
Article
ISSN
0040-4020

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✦ Synopsis


Abetract: Diethyl mesoxalate reacts with 2-and 3-vinylindoles via electrophilic substitution to give new, functionalized and annellated indoles inhigh regioselectivities. Regio-controlled dimerization processes occur in the reactions of the vinylindoles 5a and 8a. Nitrosobenzene reacts with 2-and 3-vinylindoles in a multi-stage sequence including regiospecific tandem hetero-Diels-Alder reactions to give the new, 2,3_difunctionalized indoles 11 and 12 which are