Facile Entry to 3,4-Dihydro-1H-pyrrolo[2,1-c][1,4]oxazines through the oxa-Pictet–Spengler Reaction - Université de Rennes Access content directly
Journal Articles European Journal of Organic Chemistry Year : 2016

Facile Entry to 3,4-Dihydro-1H-pyrrolo[2,1-c][1,4]oxazines through the oxa-Pictet–Spengler Reaction

C.R. Reddy
  • Function : Author
A.G. Burra
  • Function : Author
K.K. Singarapu
  • Function : Author

Abstract

An intermolecular approach to the construction of 3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazines is reported for the first time using the oxa-Pictet–Spengler reaction. The method involves a sequence of carbon–carbon- and carbon–oxygen-bond formation between a substituted 2-(1H-pyrrol-1-yl)ethan-1-ol and an aldehyde/ketone. p-Toluenesulfonic acid (pTSA) was identified as a suitable catalyst to promote the reaction. The method provides a one-step conversion of various aldehydes/ketones into the corresponding 3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazines. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Dates and versions

hal-01416444 , version 1 (14-12-2016)

Identifiers

Cite

C.R. Reddy, A.G. Burra, K.K. Singarapu, R. Grée. Facile Entry to 3,4-Dihydro-1H-pyrrolo[2,1-c][1,4]oxazines through the oxa-Pictet–Spengler Reaction. European Journal of Organic Chemistry, 2016, 2016 (31), pp.5274--5281. ⟨10.1002/ejoc.201600928⟩. ⟨hal-01416444⟩
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