Table 7 Synthesis of pyridine derivatives and 1,4-DHPs in the presence of NH₄VO₃ as the catalyst

From: Ammonium metavanadate (NH₄VO₃): a highly efficient and eco-friendly catalyst for one-pot synthesis of pyridines and 1,4-dihydropyridines

Entry	Aldehyde (1)	Product (5) Path A^a		Product (5) Path B^b		Mp (°C) ^ref Product (5)	Product (4)^c		Mp (°C) ^ref Product (4)
		Product (5) Path A^a		Product (5) Path B^b			Time (min)	Yield^d (%)
		Time (min)	Yield^d (%)	Time (min)	Yield^d (%)		Time (min)	Yield^d (%)
1	Formaldehyde	5	99	5	98	69–70⁵⁵	20	65	165–168⁵⁶
1	Formaldehyde					69–70⁵⁵			165–168⁵⁶
2	PhCHO	10	99	15	96	59–61⁵³	15	80	151–153⁵⁴
2	PhCHO					59–61⁵³			151–153⁵⁴
3	4-(Me)C₆H₄CHO	10	95	15	97	71–73²⁹	20	87	133–136⁵⁴
3	4-(Me)C₆H₄CHO					71–73²⁹			133–136⁵⁴
4	4-(OMe)C₆H₄CHO	10	100	25	96	57–58⁴⁴	10	90	163–165⁵⁴
4	4-(OMe)C₆H₄CHO					57–58⁴⁴			163–165⁵⁴
5	4-(Br)C₆H₄CHO	10	99	10	98	51–53²⁹	15	95	160–162⁵⁴
5	4-(Br)C₆H₄CHO					51–53²⁹			160–162⁵⁴
6	4-(Cl)C₆H₄CHO	10	96	10	97	71–72²⁹	20	93	144–147⁵⁷
6	4-(Cl)C₆H₄CHO					71–72²⁹			144–147⁵⁷
7	4-(F)C₆H₄CHO	10	99	15	98	88–89²⁹	20	90	153–156⁵⁸
7	4-(F)C₆H₄CHO					88–89²⁹			153–156⁵⁸
8	4-(OH)C₆H₄CHO	15	99	20	95	171–174⁴⁴	60	85	227–230⁵⁴
8	4-(OH)C₆H₄CHO					171–174⁴⁴			227–230⁵⁴
9	3-(OH)C₆H₄CHO	15	99	10	97	150–153⁵⁹	45	88	187–189⁵⁴
9	3-(OH)C₆H₄CHO					150–153⁵⁹			187–189⁵⁴
10	3-(NO₂)C₆H₄CHO	10	98	30	95	60–61⁵³	40	91	163–166⁵⁴
10	3-(NO₂)C₆H₄CHO					60–61⁵³			163–166⁵⁴
11	4-(CN)C₆H₄CHO	20	99	10	99	100–102²⁹	15	96	194–196⁶⁰
11	4-(CN)C₆H₄CHO					100–102²⁹			194–196⁶⁰
12	Furan-2-carbaldehyde	10	80	10	98	Oil	16	98	161–163⁶¹
12	Furan-2-carbaldehyde					Oil			161–163⁶¹
13	Thiophen-2-carbaldehyde	40	75	10	98	37–39⁴⁴	15	97	168–170⁵⁵
13	Thiophen-2-carbaldehyde					37–39⁴⁴			168–170⁵⁵
14	Cinnamaldehyde	10	65	25	80	161–162⁴⁴	20	98	148–150⁵⁴
14	Cinnamaldehyde					161–162⁴⁴			148–150⁵⁴
15	Terephthalaldehyde	180	83	180	90	211–213⁶²	30	97	279–283⁶³
15	Terephthalaldehyde					211–213⁶²			279–283⁶³

^aReaction conditions: aldehyde (1.0 mmol), ethyl acetoacetate (2.0 mmol), ammonium acetate (2.0 mmol), AcOH (3.0 mL), NH₄VO₃ (117.0 mg), under air condition. ^bReaction conditions: 1,4-dihydropyridines (1.0 mmol), AcOH (3.0 mL), NH₄VO₃ (117.0 mg), under air condition. ^cReaction conditions: aldehyde (1.0 mmol), ethyl acetoacetate (2.0 mmol), ammonium acetate (2.0 mmol), EtOH (3.0 mL), NH₄VO₃ (15.0 mg). ^dIsolated yields. ^eReaction conditions: aldehyde (1.0 mmol), ethyl acetoacetate (4.0 mmol), ammonium acetate (4.0 mmol), AcOH (3.0 mL), NH₄VO₃ (150.0 mg).

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