Intramolecular [4+2] cycloaddition in N-allyl- and N-propargyl-alpha-furyl lactams

Poplevin, D.S.; Nikitina, E.V.; Zaytsev, V.P.; Varlamov, A.V.; Tilve, S.G.; Zubkov, F.I.

dc.contributor.author	Poplevin, D.S.
dc.contributor.author	Nikitina, E.V.
dc.contributor.author	Zaytsev, V.P.
dc.contributor.author	Varlamov, A.V.
dc.contributor.author	Tilve, S.G.
dc.contributor.author	Zubkov, F.I.
dc.date.accessioned	2018-06-18T04:15:19Z
dc.date.available	2018-06-18T04:15:19Z
dc.date.issued	2018
dc.identifier.citation	Chemistry of Heterocyclic Compounds. 54(4); 2018; 451-457.	en_US
dc.identifier.uri	https://doi.org/10.1007/s10593-018-2290-2
dc.identifier.uri	http://irgu.unigoa.ac.in/drs/handle/unigoa/5253
dc.description.abstract	The size of nitrogen heterocycle in N-allyl- and N-propargyl-alpha-furyl lactams, as well as the nature of the unsaturated substituent linked to the nitrogen atom affected the possibility of thermal intramolecular [4+2] cycloaddition between multiple bond and the furan ring. N-Allyl-?-(alpha-furyl)butyrolactam was shown to be unreactive at temperatures from 140 to 230 degrees ?. Substituted delta-valero- and epsilon-caprolactams underwent partial Diels-Alder cyclization, forming tautomeric mixtures that contained both the initial open-chain form and the cyclic form (diastereomeric 3a,6-epoxyisoindoles fused with an aza ring) in ratios between 19:81 and 55:45. N-Propargyl-alpha-furyl lactams did not participate in thermal IMDAF reaction regardless of the ring size and the temperature of the synthesis.	en_US
dc.publisher	Springer	en_US
dc.subject	Chemistry	en_US
dc.title	Intramolecular [4+2] cycloaddition in N-allyl- and N-propargyl-alpha-furyl lactams	en_US
dc.type	Journal article	en_US
dc.identifier.impf	cs