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TfOH mediated intermolecular electrocyclization for the synthesis of pyrazolines and its application in alkaloid synthesis.

ABSTRACT: TfOH mediated easy access to interesting pyrazolines starting from an aldehyde, phenylhydrazine and styrene has been developed. The scope of this synthetic methodology has been explored by synthesizing various 1,3,5-trisubstituted pyrazolines in very good yields with very high regioselectivity. The origin of regioselectivity has been explained by comparing the stability of possible intermediate carbocations. The synthetic utility of a green solvent has been explored by synthesizing some of pyrazolines in a DES medium. The synthetic application of the present methodology is employed in the synthesis of a pyrazoline alkaloid.

SUBMITTER: Annes SB

PROVIDER: S-EPMC9085413 | biostudies-literature | 2018 Aug

REPOSITORIES: biostudies-literature

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TfOH mediated intermolecular electrocyclization for the synthesis of pyrazolines and its application in alkaloid synthesis.

Annes Sesuraj Babiola SB Vairaprakash Pothiappan P Ramesh Subburethinam S

RSC advances 20180824 53

TfOH mediated easy access to interesting pyrazolines starting from an aldehyde, phenylhydrazine and styrene has been developed. The scope of this synthetic methodology has been explored by synthesizing various 1,3,5-trisubstituted pyrazolines in very good yields with very high regioselectivity. The origin of regioselectivity has been explained by comparing the stability of possible intermediate carbocations. The synthetic utility of a green solvent has been explored by synthesizing some of pyraz ...[more]

PMID: 35546823

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