Synthesis 2020; 52(01): 127-134
DOI: 10.1055/s-0037-1610731
paper
© Georg Thieme Verlag Stuttgart · New York

Methods for the Synthesis of Piperazine Derivatives Containing a Chiral Bi-2-naphthyl Moiety

Mariappan Periasamy
School of Chemistry, University of Hyderabad, Central University P. O, Hyderabad 500046, India   Email: mpsc@uohyd.ac.in
,
Boda Venkanna
,
Miriyala Nagaraju
,
Lakavathu Mohan
› Author Affiliations
We are thankful to the DST-SERB, New Delhi for support (SB/S5/GC-01/2014) to M. P. and for the DST support to the school of chemistry under the FIST and IRPHA programs. Support of the CSIR-HRDG (No: 02/0176/14/EMR-II) to M. P. and support of the UGC under UPE and CAS programs are also thankfully acknowledged.
Further Information

Publication History

Received: 29 May 2019

Accepted after revision: 09 September 2019

Publication Date:
01 October 2019 (online)


Abstract

Piperazine derivatives containing 1,1′-bi-2-naphthyl moiety were synthesized starting from 2,2′-dimethoxy-1,1′-bi-naphthalene via acylation using ethyl chlorooxoacetate and subsequent condensation with 1,2-diamines followed by reduction of the corresponding dihydro-2-piperazinone intermediate using the NaBH4/I2 reagent system. The corresponding chiral piperazine derivatives containing bi-2-napthyl moiety was synthesized by asymmetric reduction of ethyl dimethoxy-bi-2-naphthyloxoacetate by chiral oxazoborolidine catalyst prepared in situ using S-diphenylprolinol (S-DPP), B(OCH3)3 and H3B·THF. The resulting diols were mesylated and cyclized using 1,2-diamines to obtain the corresponding chiral piperazine derivatives.

Supporting Information

 
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