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Facile Entry to 3,4‐Dihydro‐1 H ‐pyrrolo[2,1‐ c ][1,4]oxazines through the oxa ‐Pictet–Spengler Reaction
Author(s) -
Reddy Chada Raji,
Burra Amarender Goud,
Singarapu Kiran K.,
Grée René
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600928
Subject(s) - oxazines , aldehyde , chemistry , ketone , intermolecular force , catalysis , carbon fibers , medicinal chemistry , organic chemistry , molecule , mathematics , composite number , algorithm
An intermolecular approach to the construction of 3,4‐dihydro‐1 H ‐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‐(1 H ‐pyrrol‐1‐yl)ethan‐1‐ol and an aldehyde/ketone. p ‐Toluenesulfonic acid ( p TSA) 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‐1 H ‐pyrrolo[2,1‐ c ][1,4]oxazines.