2016
DOI: 10.1002/bkcs.10812
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Synthesis of Aminonaphthalenes from Morita–Baylis–Hillman Carbonates via 6π‐Electrocyclization of Ketenimine Intermediates

Abstract: Morita-Baylis-Hillman (MBH) adducts have been used extensively for the synthesis of various cyclic and acyclic compounds. 1 One of the important chemical transformations of MBH adducts starts from a conversion of electrophilic β-carbon of acrylate moiety to a nucleophilic center by forming MBH adduct-derived phosphorous ylide I, as shown in Scheme 1. 2,3 The MBH ylide I could be formed by the reaction of MBH bromide or acetate with tertiary phosphine in the presence of base, 2 and the ylide has been used for t… Show more

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Cited by 5 publications
(3 citation statements)
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“…A dipolar interaction between the sulfur atom and phosphorous atom in 2c might facilitate an abstraction of amide proton and subsequent elimination of Ph 3 PO to form a ketenimine intermediate. The ketenimine underwent 6π‐electrocyclization reaction to produce 5 , as already reported in our previous report …”
Section: Methodssupporting
confidence: 70%
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“…A dipolar interaction between the sulfur atom and phosphorous atom in 2c might facilitate an abstraction of amide proton and subsequent elimination of Ph 3 PO to form a ketenimine intermediate. The ketenimine underwent 6π‐electrocyclization reaction to produce 5 , as already reported in our previous report …”
Section: Methodssupporting
confidence: 70%
“…However, the reaction of amide ylide 2c , bearing a 2‐thienyl moiety, showed somewhat different result. The reaction of 2c and 3b afforded the desired product 4j in low yield (42%) along with benzo[ b ]thiophene 5 in appreciable amount (14%), as shown in Scheme . A dipolar interaction between the sulfur atom and phosphorous atom in 2c might facilitate an abstraction of amide proton and subsequent elimination of Ph 3 PO to form a ketenimine intermediate.…”
Section: Methodsmentioning
confidence: 97%
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