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Aminophosphonate synthesis gone wrong: X-ray identification of the products

Single-crystal X-ray analysis of three quinolin-2-yl derivatives S1-S3 formed in microwave-assisted reactions will be presented (Scheme 1). Microwave synthesis of aminophosphonate diesters yielded N-phenylquinoline-2-carboxamide (S1) and (4-aminophenyl)(quinolin-2-yl)methanone (S2) as main products, while the expected aminophosphonate diester (1) was present in the mixture in small quantities. Neat microwave reaction of quinoline-2-carboxaldehyde and aniline afforded anilinium quinoline-2-carboxylate (S3) along with the expected imine product (2). Both classical thermal synthetic procedures gave the expected aminophosphonate or the imine products in good yields without formation of the side-products S1-S3.

X-ray crystal analysis; aminophosphonate; microwave synthesis

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