Synlett 2018; 29(09): 1195-1198
DOI: 10.1055/s-0036-1591949
letter
© Georg Thieme Verlag Stuttgart · New York

l-Proline-Catalysed One-Pot aza-Diels–Alder Reaction in Water: Regioselective Synthesis of Spiro(isoxazolo[5,4-b]pyridine-5,5′-pyrimidine) Derivatives

Yuvaraj Dommaraju*
a  Applied Organic Chemistry Group, Chemical Science & Technology Division, CSIR-North-East Institute of Science and Technology, Jorhat 785006, Assam, India   Email: [email protected]   Email: [email protected]
b  Department of Chemistry, Indian Institute of Technology Bombay, Powai 400076, Mumbai, Maharashtra, India
,
Somadrita Borthakur
a  Applied Organic Chemistry Group, Chemical Science & Technology Division, CSIR-North-East Institute of Science and Technology, Jorhat 785006, Assam, India   Email: [email protected]   Email: [email protected]
,
Dipak Prajapati*
a  Applied Organic Chemistry Group, Chemical Science & Technology Division, CSIR-North-East Institute of Science and Technology, Jorhat 785006, Assam, India   Email: [email protected]   Email: [email protected]
› Author Affiliations
We thank CSIR, New Delhi for financial support to this work under network project. YD thanks UGC, New Delhi for the award of a ­research fellowship.
Further Information

Publication History

Received: 05 February 2017

Accepted after revision: 11 February 2018

Publication Date:
20 March 2018 (online)


Abstract

A simple and efficient l-proline-catalysed synthesis of spiro(isoxazolo[5,4-b]pyridine-5,5′-pyrimidine) derivatives in water has been accomplished through a pseudo five-component one-pot domino aza-Diels–Alder reaction involving 3-amino crotanonitrile, hydroxylamine hydrochloride, aromatic aldehydes and barbituric acids. The main advantages of the present method are mild reaction conditions, modest purification process involving no chromatographic techniques and high yields. The protocol is a good alternative to prepare spiro derivatives with readily available starting materials, which makes the method highly attractive.

Supporting Information

 
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