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; Somadrita Borthakur; Dipak Prajapati

doi:10.1055/s-0036-1591949

Synlett, Inhaltsverzeichnis

Synlett 2018; 29(09): 1195-1198
DOI: 10.1055/s-0036-1591949

letter

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*

^aApplied Organic Chemistry Group, Chemical Science & Technology Division, CSIR-North-East Institute of Science and Technology, Jorhat 785006, Assam, India eMail: dr_yuvarajd@yahoo.com eMail: dr_dprajapati2003@yahoo.co.uk

^bDepartment of Chemistry, Indian Institute of Technology Bombay, Powai 400076, Mumbai, Maharashtra, India

,

Somadrita Borthakur

^aApplied Organic Chemistry Group, Chemical Science & Technology Division, CSIR-North-East Institute of Science and Technology, Jorhat 785006, Assam, India eMail: dr_yuvarajd@yahoo.com eMail: dr_dprajapati2003@yahoo.co.uk

,

Dipak Prajapati*

^aApplied Organic Chemistry Group, Chemical Science & Technology Division, CSIR-North-East Institute of Science and Technology, Jorhat 785006, Assam, India eMail: dr_yuvarajd@yahoo.com eMail: dr_dprajapati2003@yahoo.co.uk

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Abstract

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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.

Key words

heterocycles - multicomponent reaction - spiro compounds - aqueous medium - aza-Diels–Alder reaction

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References and Notes

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12 General Procedure for the Synthesis of Spiro(isoxazolo[5,4-b]pyridine-5,5′-pyrimidines) 5a–l: 3-Aminocrotanonitrile (1; 2 mmol), hydroxylamine hydrochloride (2; 2 mmol) were taken in 50-mL round-bottomed flask. To this were added l-proline (30 mol%) and H₂O (10 mL) and the mixture was stirred at reflux for 10 min. Then barbituric acid (3; 2 mmol) and aromatic aldehyde 4 (4 mmol) were added and the reaction mixture was stirred for 60 min. Upon completion of the reaction (monitored by TLC) the reaction mixture was cooled to r.t. and filtered to give the crude products, which were further purified by recrystallization from 95% EtOH to obtain the analytically pure 5 as a product. 1′,3,3′-Trimethyl-4,6-diphenyl-6,7-dihydro-2′H,4H-spiro(isoxazolo[5,4-b]pyridine-5,5′-pyrimidine)-2′,4′,6′(1′H,3′H)-trione (5a): white solid; mp 185–186 °C (177–178 °C^13c). ¹H NMR (300 MHz, CDCl₃): δ = 7.26 (ddd, J = 16.5, 10.9, 6.3 Hz, 8 H), 7.04 (d, J = 5.7 Hz, 2 H), 5.26 (d, J = 3.5 Hz, 1 H), 5.10 (d, J = 4.1 Hz, 1 H), 4.91 (s, 1 H), 2.98 (s, 3 H), 2.80 (s, 3 H), 1.70 (s, 3 H). ¹³C NMR (75 MHz, CDCl₃): δ = 170.03, 165.67, 164.78, 158.48, 149.61, 134.65, 129.82, 129.02, 128.74, 128.63, 127.12, 91.00, 64.70, 58.62, 47.92, 28.42, 27.67, 11.67. IR (KBr): 3185, 2998, 2926, 1751, 1687, 1651, 1615, 1537, 1510, 1482, 1381, 1160, 840, 775 cm^–1. MS (ESI): m/z = 431.2 [M + H]⁺.

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